Month: June 2021

Reference of 202925-10-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 202925-10-8, name is (4-Chloro-3-fluorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Example 229 4- ( (4-Chloro-3-fluorobenzyl) oxy) -1- (2-ethyl-l-methyl-lH- benzimidazol-6-yl) yridin-2 ( 1H) -one To a solution of 1- (2-ethyl-l-methyl-lH-benzimidazol-6- yl) -4-hydroxypyridin-2 ( 1H) -one (500 mg) , (4-chloro-3- fluorophenyl) methanol (596 mg) and tributylphosphine (1.13 g) in THF (20 ml) was added 1, 1′ – (azodicarbonyl) dipiperidine (1.41 g) , and the reaction mixture was stirred at 60C for 2 h. The reaction mixture was cooled to room temperature. The mixture was poured into water and extracted with EtOAc. The extract was washed with brine, dried over MgS04, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH) . ‘The resulting solid was recrystallized from EtOH-water to give the title compound (265 mg) as a white solid. MS (ESI+) : [M+H] + 412.3. 1H NMR (400 MHz, DMSO-d6) : delta 1.33 (3H, t, J = 7.5 Hz), 2.90 (2H, q, J = 7.5 Hz), 3.74 (3H, s) , 5.18 (2H, s), 5.97 (1H, d, J = 2.6 Hz), 6.12 (1H, dd, J = 2.4, 7.5 Hz), 7.07 (1H, d, J = 8.4 Hz), 7.35 (1H, d, J = 8.5 Hz), 7.52-7.57 (2H, m) , 7.60 (2H, dd, J = 4.8, 7.8 Hz), 7.66 (1H, t, J = 8.2 Hz).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 202925-10-8, (4-Chloro-3-fluorophenyl)methanol.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); A1;,
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Reference of 612-16-8 ,Some common heterocyclic compound, 612-16-8, molecular formula is C8H10O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: In a round-bottom flask, benzylic alcohol 1a (10 mmol, 2.0 equiv.), benzenesulfonyl chloride 2a (13 mmol, 1.3 equiv.) and NMP (2.5 equiv.). Then, DCE (3 mL) were added. The mixture was stirred at 80 C for 1.5 h. After completion of the reaction (monitoredby TLC), water (10 mL) was added and the mixture was extracted with ethyl acetate (3*10 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel to give the desired alkyl chlorides 3.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 612-16-8, (2-Methoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zheng, Dagui; Mao, Liu-Liang; Zhu, Xian-Hong; Zhou, An-Xi; Synthetic Communications; vol. 48; 21; (2018); p. 2793 – 2800;,
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Electric Literature of 530-91-6 , The common heterocyclic compound, 530-91-6, name is 1,2,3,4-Tetrahydronaphthalen-2-ol, molecular formula is C10H12O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a stuffed solution of 1,2,3,4-tetrahydronaphthalen-2-ol (250 mg, 1.68 mmol) in DCM (5 mL) was added triethylamine (1.17 mL, 8.50 mmol) at 0 C followed by addition of mesyl chloride (0.26 mL, 3.35 mmol). The reaction mixture was then stirred at 0 C for 2 h. The reaction was monitored by ?H NMR. After completion of reaction, the mixture was quenched with ice, and extracted with DCM (2×50 mL). The combined organic layer was dried over sodium sulfate and concentrated to afford 340 mg of 1 ,2,3,4-tetrahydronaphthalen- 2-yl methanesulfonate as a brown liquid which was taken to the next step without further purification.

The synthetic route of 530-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; GREEN, Michael, John; PHAM, Son, Minh; PUJALA, Brahmam; AGARWAL, Anil, Kumar; NAYAK, Ajan, Kumar; KHARE, Sweta; GUGULOTH, Rambabu; RANDIVE, Nitin, Atmaram; WO2015/58084; (2015); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 597-31-9, name is 3-Hydroxy-2,2-dimethylpropanal, molecular formula is C5H10O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of 3-Hydroxy-2,2-dimethylpropanal

116 parts by mass of pentaerythritol was dissolved in 1800 parts by mass of water, and methanesulfonic acid (a product of Wako Pure Chemical Industries Ltd.) was added thereto to make the resultant solution at pH 1.6. To the solution, 290 parts by mass of the HPA aqueous solution A prepared in Production Example 2 was added dropwise over 3 hours. A reaction temperature was set to 90 C. After completing the dropwise addition, the resultant solution was aged at 90 C. for 12 hours. After completing the aging, the resultant reaction solution was divided into 765 parts by mass and 1441 parts by mass, and the 1441 parts by mass of the reaction solution was solid-liquid separated to obtain 183 parts by mass of wet spiroglycol and 1130 parts by mass of a filtrate. Thereafter, the thus obtained wet spiroglycol was neutralized and washed with 500 parts by mass of a 500 ppm sodium hydroxide aqueous solution, and subsequently the resultant was washed with 500 parts by mass of water. Thereafter, the spiroglycol was dried. Incidentally, the 765 parts by mass of the reaction solution also contains spiroglycol crystals, and the spiroglycol crystals work as a seed crystal in the reaction of the subsequent second and later cycles. (Second to Fifteenth Cycles of Spiroglycol Synthesis) (0159) 765 parts by mass of the reaction solution obtained in the reaction of the first cycle, 1000 parts by mass of the filtrate obtained in the reaction of the first cycle, 25 parts by mass of water, 116 parts by mass of pentaerythritol and 0.7 parts by mass of methanesulfonic acid were mixed. Here, the resultant solution had pH 1.6. To this solution, 290 parts by mass of the HPA aqueous solution A was added dropwise over 3 hours. A reaction temperature was set to 90 C. After completing the dropwise addition, the resultant was aged at 90 C. for 3 hours. After completing the aging, the resultant reaction solution was divided into 765 parts by mass and remaining 1431.7 parts by mass, and the 1431.7 parts by mass of the reaction solution was solid-liquid separated to obtain 244 parts by mass of wet spiroglycol and 1083 parts by mass of a filtrate. (0160) Then, also in the reaction of the third and later cycles, the reaction was repeatedly performed by mixing 765 parts by mass of the reaction solution obtained in the previous cycle, 1000 parts by mass of the filtrate, 25 parts by mass of water, 116 parts by mass of pentaerythritol and 0.7 parts by mass of methanesulfonic acid, and adding 290 parts by mass of the HPA aqueous solution A dropwise thereto over 3 hours. In the reaction of each cycle, about 80 to 90% by mass of the mother liquor of the whole reaction solution obtained in the previous cycle was used in the reaction of the next cycle. This synthesis reaction was repeatedly performed, and a stable mother liquor composition was obtained. In the reaction of the fifteenth cycle, the dried spiroglycol was obtained in an amount of 236 parts by mass in total. The yield of the spiroglycol based on the charged pentaerythritol (excluding the pentaerythritol contained in the filtrate) was 91.7% by mol.The same synthesis as that of Reference Example 5 was performed by mixing 765 parts by mass of the reaction solution obtained in the reaction of the fifteenth cycle of Reference Example 5, 1000 parts by mass of the filtrate, 25 parts by mass of water, 116 parts by mass of pentaerythritol and 0.7 parts by mass of methanesulfonic acid, and adding 290 parts by mass of the HPA aqueous solution A dropwise thereto over 3 hours (corresponding to the first cycle of SPG synthesis illustrated in FIGS. 1 and 2). Then, 765 parts by mass of the reaction solution obtained by the reaction of this first cycle was used and mixed with 1000 parts by mass of the filtrate, 25 parts by mass of water, 116 parts by mass of pentaerythritol and 0.7 parts by mass of methanesulfonic acid, and 290 parts by mass of the HPA aqueous solution A was added dropwise over 3 hours to repeatedly perform the synthesis reaction of spiroglycol. This spiroglycol synthesis reaction was further repeated until an impurity concentration in the resultant spiroglycol was stabilized. (0163) The gas chromatographic purity of the spiroglycol obtained in the eleventh cycle of the SPG synthesis was found to be 99.58 area % of spiroglycol, with 0.01 area % of dioxane triol monoformal, 0.11 area % of hydroxypivalaldehyde neopentyl glycol acetal and 0.14 area % of spiro monoalcohol. The results are shown in Table 1. Besides, the transition of the impurity concentration in the spiroglycol is illustrated in FIGS. 1 and 2.

With the rapid development of chemical substances, we look forward to future research findings about 597-31-9.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; YAMANE, Masahiro; (16 pag.)US2019/55259; (2019); A1;,
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Synthetic Route of 112-27-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 112-27-6, name is 2,2′-(Ethane-1,2-diylbis(oxy))diethanol, molecular formula is C6H14O4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: Oligo ethylene glycol (2 eq, 40 mmol) was dissolved intetrahydrofuran (20 mL) at 0 oC. Sodium hydroxide (1.5 eq,30 mmol, 1.2 g) in 15 mL H2O was added drop wise to thesolution of oligo ethylene glycol. After stirring for 30 min, ptoluenesulfonylchloride (1 eq, 20 mmol, 3.8 g) was dissolvedin tetrahydrofuran (15 mL) at 0 oC. Oligoethyleneglycol was added drop wise in the solution of ptoluenesulfonylchloride. After the addition was completed,the aqueous solution was treated with HCl 10% and extractedwith dichloromethane. The organic layer was washedwith distilled water and dried over MgSO4. After the solventwas removed, the residue was purified by column chromatography(ethyl acetate/n-hexane = 1:1 v/v)

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 112-27-6, 2,2′-(Ethane-1,2-diylbis(oxy))diethanol.

Reference:
Article; Lari, Jalil; Moradgholi, Fatemeh; Vahedi, Hooshang; Massoudi, Abdolhossein; Letters in Organic Chemistry; vol. 12; 9; (2015); p. 668 – 673;,
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Reference of 627-30-5 ,Some common heterocyclic compound, 627-30-5, molecular formula is C3H7ClO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A 500 mL three-necked flask was charged with a magnetic stirrer and a thermometer, and 5.2 g of p-toluenesulfonic acid (0.03 mol) was added thereto.94.5 g of 3-chloropropanol (1.0 mol), 200 mL of dichloromethane, and 16.2 g of 3,4-dihydropyran (1.5 mol) were stirred at room temperature 20-25 C for 1 h.After the reaction liquid was subjected to gas chromatography to detect 3-chloropropanol, 100 mL of water was added to the system.After stirring for 5 min, the phases were separated, and the organic phase was washed with 100 mL of brine, dried over anhydrousDistillation under reduced pressure, collecting 110-115 C fraction (vacuum degree 30 mbar),A colorless transparent liquid of 164.6 g, which is 2-(3-chloropropoxy)tetrahydro-2H-pyran, has a GC content of 98.2% and a yield of 91.13%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,627-30-5, its application will become more common.

Reference:
Patent; Hunan Youse Chenzhoufu Chemical Co., Ltd.; Wang Gang; Peng Zhimin; Liu Bin; Li Jun; Li Zhipeng; Su Wanli; Zhang Zhenhua; (11 pag.)CN109336740; (2019); A;,
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Electric Literature of 29683-23-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 29683-23-6, name is Tetrahydro-2H-thiopyran-4-ol. A new synthetic method of this compound is introduced below.

To a solution of tetrahydro-2H-thiopyran-4-ol 17 (46.00 g, 0.390 mol), DMAP (0.48 g, 1 mol%) and pyridine (33.93 g, 0.429 mol) in dry dichloromethane (500 mL) tosyl chloride (81.70 g, 0.429 mol) was added at 0 FontWeight=”Bold” FontSize=”10″ . The reaction mixture was stirred for 8 hours at room temperature following by washing with 5% HCl (2×200 mL) and brine (100 mL). Organic layer was dried over sodium sulfate and concentrated in vacuo. Yield: 92.00 g (87%), mp 92-94 FontWeight=”Bold” FontSize=”10″ , Rf 0.67 (ethyl acetate : hexane, 1 : 1). 1 NMR (500 MHz, CDCl3) delta7.79 (1, d, J= 8.1 Hz, H-Ar), 7.34 (1, d, J= 8.1 Hz, H-Ar), 4.62-4.56 (1, m, H-4), 2.84-2.78 (2, m, H-3b,5b), 2.52-2.46 (2, m, H-3a,5a), 2.45 (3, s, 3), 2.06-2.00 (2H, m, H-2b,6b), 1.97-1.91 (2, m, H-2a,6a). 13CNMR(125 MHz, CDCl3) delta144.87(-Ar), 130.16(-Ar),130.02(-Ar),127.74 (-Ar),45.18 (-4),33.22 (-3,5),25.13 (-2,6),21.79 (3).Elemental analysis calculated for C12H16O3S2, C, 52.92; H, 5.92; S, 23.54; found C, 53.11; H, 5.78; S, 23.29%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29683-23-6, Tetrahydro-2H-thiopyran-4-ol, and friends who are interested can also refer to it.

Reference:
Article; Chabanenko, Roman M.; Yu. Mykolenko, Svitlana; Kozirev, Eugene K.; Palchykov, Vitalii A.; Synthetic Communications; vol. 48; 17; (2018); p. 2198 – 2205;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 7287-81-2, name is 1-(m-Tolyl)ethanol. A new synthetic method of this compound is introduced below., Safety of 1-(m-Tolyl)ethanol

The racemic alcohol (1r) at -30 C1.0 mmol as a catalyst was dissolved in 5 ml dichloromethane (wherein, R I andn is 2; and pharmaceutically acceptable salts thereof) compound of the formula(1) was added 0.01 mol% and the potassium fluoro one equivalent of fluoride, acarboxylic acid group and the ion exchange resin 80 mg silylating agent offormula (5), including (in the formula, R is methyl) was added to 0.7equivalents, and then the mixture was stirred for 1 hour. Filtering the mixturewas concentrated and then to recover the potassium fluoride and the ionexchange resin. The residue was purified by flash chromatography (acetone /hexane / triethylamine = 1: 5: 0.025) to give the chiral alcohol; to give the(2r, yield 47% 98% ee, (R) -form).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 7287-81-2, 1-(m-Tolyl)ethanol.

Reference:
Patent; RESEARCH & BUSINESS FOUNDATION SUNGKYUNKWAN UNIVERSITY; SONG, CHOON GEUI; PARK, SANG YEON; LEE, JI WOONG; (43 pag.)KR2015/114445; (2015); A;,
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Reference of 217479-60-2, Adding some certain compound to certain chemical reactions, such as: 217479-60-2, name is 2,4,6-Trichlorobenzyl alcohol,molecular formula is C7H5Cl3O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 217479-60-2.

To a stirred solution of 2,4,6-trichlorobenzylalcohol (10.0 g; 47.3 mmoles) in chloroform (100 ml) kept under nitrogen atmosphere, thionyl chloride (6.07 mL, 85.1 mmole) was added slowly at 0 C. over a period of 15 minutes followed by catalytic amount of DMF. The reaction mix was allowed to stir at ambient temp for 3 hours. The reaction mixture was quenched with 50 mL of water; the aqueous layer was extracted with DCM (3*100 ml). The combined organic layer was washed with 5% sodium bicarbonate solution (2*50 ml) followed by brine (50 ml) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. 10.9 g (100.0% of theory) of 1,3,5-trichloro-2-chloromethyl-benzene was obtained in form of a white solid. 1HNMR (CDCl3, 400 MHz): delta=7.37 (2H, s); 4.82 (2H, s) Mass: M=229.8

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 217479-60-2, 2,4,6-Trichlorobenzyl alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA CROP PROTECTION LLC; US2011/230537; (2011); A1;,
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Application of 31775-67-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 31775-67-4, name is trans-2-Aminocyclopentanol hydrochloride. A new synthetic method of this compound is introduced below.

A mixture of methyl 5-bromo-3-chloro-2-hydroxy-4- methylbenzoate (2.90 g) , trans-2-aminocyclopentanolhydrochloride (2.84 g) and triethylamine (4.20 g) inmethanol/dichloromethane was stirred with heating under reflux for 3 days. The reaction mixture was concentrated, andpurified by silica gel column chromatography (ethylacetate/petroleum ether) to give the title compound (1.70 g) .1H NMR (400 MHz, CDC13) delta 1.65-1.95 (4H, m) , 2.02-2.10 (1H, m) , 2.25-2.35 (1H, m) , 2.55 (3H, s) , 3.55 (1H, brs), 4.02-4.12 (2H, m) , 6.45 (1H, brs), 7.51 (1H, s) . 1H was not observed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31775-67-4, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
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