Category: alcohols-buliding-blocks

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. 111-90-0, name is Diethylene Glycol Monoethyl Ether. A new synthetic method of this compound is introduced below., 111-90-0

Diethylene glycol monoethyl ether (1 equiv.) and water (1 mL) were mixed together and stirred on ice before addition of NaOH (2.95 equiv.) and 0.4 M tetrabutylammonium hydroxide (aq) (0.05 equiv.). Once the mixture returned to 0C, epichlorohydrin (2.95 equiv.) was added portion-wise over 3 mm. The mixture was stirred at room temperature for 16 hours. H20 (15 mL) was added and the mixture was extracted with EtOAc (4x 30 mL). The combined extracts were washed with brine (30 mL) and dried over Na2SO4. The extracts were concentrated under reduced pressure. The residue was distilled under vacuum, providing a as a colorless liquid boiling at 110-117C (0.1 mmHg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111-90-0, Diethylene Glycol Monoethyl Ether, and friends who are interested can also refer to it.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE BORDEAUX; INSTITUT POLYTECHNIQUE DE BORDEAUX; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; LECOMMANDOUX, Sebastien, Jean, Marie; GARANGER, Elisabeth, Beatrice, Michele; DEMING, Timothy; (40 pag.)WO2017/21334; (2017); A1;,
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647-42-7, A common compound: 647-42-7, name is 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol,molecular formula is C8H5F13O, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Into a 2 L four-necked flask equipped with a stirrer, a thermometer and a cooling tube,800 g (2.2 mol) of FA-6 (manufactured by Unimartech) and 175.78 g (4.4 mol) of granular NaOH (manufactured by Wako Pure Chemical Industries, Ltd.) were added. Under a nitrogen atmosphere, while stirring at 200 rpm with a Teflon (registered trademark) 12 cm crescent stirring blade, the temperature was heated to 60 C. in the flask.398.73 g (3.3 mol) of allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise thereto over 2 hours. After completion of the dropwise addition, the mixture was stirred at 70 C. for 1 hour and at 80 C. for 1 hour.Thereafter, the temperature was raised to 130 C. to remove excess allyl bromide.After cooling to 60 C., 800 g of ion-exchanged water was added, stirred for 30 minutes, then allowed to stand to separate the layers.The upper aqueous layer was withdrawn, 800 g of ion-exchanged water was added, and the mixture was stirred again, allowed to stand still and the aqueous layer was removed. Dehydrated at 60 C./5 KPa and distilled at 100 C./2 KPa to obtain 774.9 g of C 6 F 13 –CH 2 CH 2 –O – CH 2 CHCH 2 (yield 88%) as a fraction.

With the rapid development of chemical substances, we look forward to future research findings about 647-42-7.

Reference:
Patent; KAO CORP; ??????; IIDA MASAYUKI; Iida Masayuki; SHINBO AYUMI; Susumu Kuni Ayumi; (15 pag.)JP2016/121094; (2016); A;,
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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 78573-45-2, name is 3-(3-(Trifluoromethyl)phenyl)propan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. 78573-45-2

Step 3: Preparation of Compound III (i.e., 3-(3-trifluoromethylphenyl)propanal) To a solution of 10 g (48 mmol) of Compound VII, 76.6 mg of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy free radical) and 234 mg of potassium bromide in 70 mL methylene chloride was added 220 mL (pH=9.5) of sodium hypochlorite solution over 20 minutes at 10-15 C. with stirring. After five minutes of additional stirring, the organic layer was separated. The aqueous layer was extracted twice with 40 mL of methylene chloride, and the collected organic layers were dried and evaporated to yield 10 g of crude Compound III as a yellowish liquid. Yield: 100%; purity (determined by GC): 90.3%, contains 8.25% of Compound NMR data (200 MHz, CDCl3, ppm): 2.81 (t, 2H), 3.00 (t, 21-1), 7.37-7.46 (m, 4H), 9.80 (s, 1H).

Statistics shows that 78573-45-2 is playing an increasingly important role. we look forward to future research findings about 3-(3-(Trifluoromethyl)phenyl)propan-1-ol.

Reference:
Patent; Medichem, S.A.; US2010/267988; (2010); A1;,
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505-10-2, Adding a certain compound to certain chemical reactions, such as: 505-10-2, 3-(Methylthio)propan-1-ol, 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, 505-10-2, blongs to alcohols-buliding-blocks compound.

The alcohol 5-a (200 g, 1900 mmol) was dissolved in CH2C12 (2000 ml). The mixture was cooled to 0C. The w-CPBA 85% in water (970 g, 5700 mmol) was added portion wise keeping the temperature between 0 to 5C. After addition, the mixture was allowed to warm to 25C and stirred for 15 h. The mixture was filtered through a celite pad. The filtrate was purified by flash column (Eluent: petroleum ether: ethyl acetate = 3 : 1 and then ethyl acetate: methanol = 10: 1) to yield the intermediate 5-b (75 g, 29%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,505-10-2, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80447; (2012); A1;,
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107-75-5, 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. 107-75-5, name is 7-Hydroxy-3,7-dimethyloctanal. A new synthetic method of this compound is introduced below.

Compound 33: 7-hyroxycitronellal (140 mu, 0.75 mmol), Cu(OTf)2 (2.2 mg, 2.5 mol ethanethiol (108 mu, 1.5 mmol) and 1,3,5- trimethoxybenzene (42 mg, 0.25 mmol) were reacted according to method A. The mixture was stirred for 2 h at room temperature. The residual material was purified by column chromatography (silica gel 40-60, hexane / ethyl acetate 80:20) affording compound 33 (68 mg, 71% yield) as a thick oil. Characterization data of compound 33: lH NMR (CDCl3/400 MHz): delta 6.12 (s, 1H), 6.09 (s, 1H), 4.54 – 4.46 (m, 1H), 3.80 (s, 3H), 3.78 (s, 6H), 2.51 – 2.32 (m, 3H), 1.96 – 1.84 (m, 1H), 1.56 – 1.47 (m, 1H), 1.40 – 1.32 (m, 4H), 1.24 – 1.19 (m, 5H), 1.17 (s, 3H), 1.15 (s, 3H), 0.82 (t, J = 4.5 Hz, 3H); 13C NMR (CDCl3/100 MHz): delta 160.2, 159.8, 158.2, 112.4, 111.4, 91.7, 90.3, 71.0, 55.9, 55.7, 55.2, 44.2, 41.3, 38.1, 37.1, 31.4, 29.1, 26.3, 21.6, 20.0, 19.4, 15.0; HRMS (ESI): m/z calcd for C2iH3604S [M+Na]+ 407.2227 found 407.2218.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,107-75-5, 7-Hydroxy-3,7-dimethyloctanal, and friends who are interested can also refer to it.

Reference:
Patent; B. G. NEGEV TECHNOLOGIES AND APPLICATIONS LTD., AT BEN-GURION UNIVERSITY; PAPPO, Doron; PARNES, Regev; (87 pag.)WO2016/132355; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.647-42-7, name is 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol, molecular formula is C8H5F13O, molecular weight is 364.1, as common compound, the synthetic route is as follows.647-42-7

[0087] 2-(Perfluorohexyl)ethanol (18.2 g, 50 mmol) was added to toluene, and potassium hydroxide (3.5 g)/water (3.5 ml) was added to the mixture. Under ice-cooled condition, acrylic acid tert-butyl ester (10.3 ml, 70 mmol) and tetrabutylammonium bromide (1.61 g, 5 mmol) were added, and the mixture was stirred at room temperature for 3 hours. The reaction was quenched by addition of dilute hydrochloric acid. The mixture was separated in an ethyl acetate/water system, and the resulting liquid was concentrated with a rotary evaporator. After column purification, purified ester (7b; 19.0 g, yield 77%) was obtained.

Statistics shows that 647-42-7 is playing an increasingly important role. we look forward to future research findings about 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol.

Reference:
Patent; FUJIFILM Corporation; MIZUMURA Masatoshi; KATOH Shunya; UEMURA Minoru; ISHIWATAYasuhiro; YOSHIKAWA Masaru; MATSUYAMA Hiroshi; EP2738155; (2014); A1;,
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2854-16-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.2854-16-2, name is 1-Amino-2-methylpropan-2-ol, molecular formula is C4H11NO, molecular weight is 89.14, as common compound, the synthetic route is as follows.

j0086J To a 15 L glass reactor purged with nitrogen was charged Compound 14 (1.038 kg, 2.47 mol, 1 eq), followed by Me-THF (6.176 kg) and DIEA (0.384 kg, 2.97 mol, 1.2 eq). The resulting mixture was stirred at room temperature and then 1-amino-2-methylpropan-2-ol(0.265 kg, 2.97 mol, 1.2 eq) in Me-THF (2.647 kg) was slowly charged while maintaining 20-30 ¡ãC. After the reaction was complete, water (2.6 L) and n-heptane (2.076 kg) were added. The mixture was stirred for 20 mm., the aqueous layer was removed, water (2.6 L) was added and the pH of the aqueous phase adjusted to 7 using 0.1N HC1. The aqueous layer was removed, and the organic layer was washed with water (2 x 2.6 L), 4percent NaHCO3 (1.1 L), and water (1.15 L). The organic layer was concentrated under vacuum to 3.4 L. Me-THF (4.950 kg) was added, and the mixture was concentrated to 3.4 L. The residue was diluted with Me-THF (4.931 kg). The solution was clarified through a 1.2 t in-line filter. The clarified solution was concentrated to 2.6 L. The residue was heated to 45 ¡ãC, and then n-heptane (2.599 kg) was added slowly while maintaining 45 ¡ãC. The batch was seeded with 2-methyl-i -((4-(6-(trifluoromethyl)pyridin-2-yl)- 6-((2-(trifluoromethyl)pyridin-4-yl)amino)- 1,3,5 -triazin-2-yl)amino)propan-2-ol (lOg). nHeptane (2.599 kg) was added slowly while maintaining 45 ¡ãC. After ih, the batch was cooled down to 20 ¡ãC. The mixture was stirred at 20 C for ih. The batch was filtered. The solids were washed with n-heptane (2 x 1 L), and then vacuum-dried at 35 ¡ãC in an oven for 20 h. Isolated yield: 1.124 kg of 2-methyl-i -((4-(6-(trifluoromethyl)pyridin-2-yl)-6-((2- (trifluoromethyl)pyridin-4-yl)amino)- 1,3,5 -triazin-2-yl)amino)propan-2-ol (96 percent) as a light yellow powder.

Statistics shows that 2854-16-2 is playing an increasingly important role. we look forward to future research findings about 1-Amino-2-methylpropan-2-ol.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; ZHANG, Shijie; (47 pag.)WO2017/24134; (2017); A1;,
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517-21-5, Adding a certain compound to certain chemical reactions, such as: 517-21-5, Sodium 1,2-dihydroxyethane-1,2-disulfonate, 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, 517-21-5, blongs to alcohols-buliding-blocks compound.

6-Methylquinoxaline; A solution of 3,4-diaminotoluene (Aldrich, 100 g, 0.82 mol) in 600 mL of hot water (temp. 70-75 C.) was added rapidly to a 60 C. slurry of glyoxal-sodium bisulfite adduct (Aldrich, 239.5 g, 0.9 mol, 1.1 eq) in 400 mL of water. The resulting dark-brown clear solution was heated at 60 C. for 1 hr, then 5 g (0.02 mol) of additional glyoxal adduct was added. The mixture was allowed to cool to r.t. and filtered through a paper filter. The filtrate was neutralized with 5 M aq. NaOH to pH 7.5-7.8 and then extracted with ether (4¡Á400 mL). The extract was dried over Na2SO4 and concentrated on a rotary evaporator to afford 92 g of brown oil which was distilled in vacuum (bp. 100-102 C. at 10 mm Hg; Cavagnol, J. C.; Wiselogle, F. Y. J. Am. Chem. Soc. 1947, 69, 795; 86 C. at 1 mm Hg). Yield 89 g (75%) as a pale-yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,517-21-5, its application will become more common.

Reference:
Patent; Wyeth; US2005/282820; (2005); A1;,
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In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 56-81-5 as follows., 56-81-5

4.2.7 cis-2-Phenyl-1,3-dioxan-5-ol (18) Concentrated sulfuric acid (3 drops) was added to a mixture of glycerol (44 mL, 55 g, 0.60 mol) and freshly distilled benzaldehyde (48 mL, 50 g, 0.47 mol) in toluene (69 mL). The resulting mixture was heated to reflux in a Dean-Stark water separator. When the separation of water was complete (8.5 mL), the reaction mixture was allowed to cool to room temperature and the solvent removed in vacuo. The resulting white solid was recrystallized from isopropyl ether/petroleum ether. The precipitate was filtered off and purified by flash column chromatography (? = 6 cm, h = 15 cm, V = 50 mL, cyclohexane/ethyl acetate = 2:1, Rf = 0.16) to give 18 as colorless solid (42.6 g, 0.24 mol, 50% yield). Mp = 81 C; 1H NMR (DMSO-d6): delta [ppm] = 3.48-3.52 (m, 1H, OCH2CHOH), 3.91-3.97 (m, 2H, OCH2CHOH), 4.01-4.07 (m, 2H, OCH2CHOH), 4.99 (d, J = 4.8 Hz, 1H, OH), 5.53 (s, 1H, CHPh), 7.33-7.40 (m, 3H, 3′-Hphenyl, 4′-Hphenyl, 5′-Hphenyl), 7.42-7.47 (m, 2H, 2′-Hphenyl, 6′-Hphenyl); 13C NMR (DMSO-d6): delta [ppm] = 62.4 (1C, OCH2CHOH), 71.4 (2C, OCH2CHOH), 100.2 (1C, CHPh), 126.2 (2C, C-2’phenyl, C-6’phenyl), 127.9 (2C, C-3’phenyl, C-5’phenyl), 128.5 (1C, C-4’phenyl), 138.9 (1C, C-1’phenyl); IR (neat): [cm-1] = 3271, 2916, 2851, 1450, 1385, 1339, 1277, 1153, 1084, 995, 976, 806, 741, 694; HRMS (m/z): [M+H]+ calcd for C10H13O3, 181.0859; found, 181.0878; HPLC (method 1): tR = 11.7 min, purity 95.4%.

The chemical industry reduces the impact on the environment during synthesis 56-81-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Tangherlini, Giovanni; Torregrossa, Tullio; Agoglitta, Oriana; Koehler, Jens; Melesina, Jelena; Sippl, Wolfgang; Holl, Ralph; Bioorganic and Medicinal Chemistry; vol. 24; 5; (2016); p. 1032 – 1044;,
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456-47-3 , The common heterocyclic compound, 456-47-3, name is 3-Fluorobenzyl alcohol, molecular formula is C7H7FO, 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: A solution of acetonitril (10 mL, 1mmol) and periodic acid was placed in flask and stir for the 15 min. Then, a mixture of alcohols (1mmol) and S-COCC (1%mmol) was added and the resulting mixture was stirred at room temperature for a suitable period (Table 3) and completion of the reaction investigated byTLC (n-hexane/EtOAc; 2:1) analysis. Then, EtOAc (20ml) was subjoined to the reaction mixture and after being washed with water/sodium solfite (1:1), the mixture was filtered off. The solvent was vaporized and produced pure products.

According to the analysis of related databases, 456-47-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shiri, Lotfi; Sheikh, Davood; Sheikhi, Masoome; Revue Roumaine de Chimie; vol. 59; 10; (2014); p. 825 – 834;,
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