Category: alcohols-buliding-blocks

Application of 626-95-9, 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. 626-95-9, name is 1,4-Pentanediol. A new synthetic method of this compound is introduced below.

Referential Example 2: 4-(t-Butyldiphenylsilyloxy)-1-methyl-1-butanol In N,N-dimethylformamide (200 ml) were dissolved 1,4-pentanediol (10.0 g, 96.0 mmol) and imidazole (6.6 g, 96.9 mmol).. Under ice cooling, t-butyl chlorodiphenylsilane (25.2 ml, 96.4 mmol) was added dropwise.. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 2 days.. To the reaction mixture was added diethyl ether, followed by washing with water.. The organic layer was dried over anhydrous magnesium sulfate.. After filtration, the residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (32.0 g, 97%) was obtained as a colorless oil. IR (ATR) nu: 3350, 2929, 2856, 1427, 1105, 822, 739, 698, 609, 501 cm-1.1H-NMR (400MHz, CDCl3) delta: 1.05(9H,S), 1.19(3H,d,J=6.3Hz), 1.46-1.72(4H,m), 2.02-2.08(1H,m), 3.69(2H,t,J=6.0Hz), 3.78-3.90(1H,m), 7.30-7.50(6H,m), 7.62-7.88(4H,m). MS (m/z): 343 (M++H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,626-95-9, 1,4-Pentanediol, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
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Application of 55977-10-1, 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. 55977-10-1, name is 3-Bromo-7-hydroxy-4-methylchromen-2-one, molecular formula is C10H7BrO3, 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.

A mixture of 3-bromo-7-hydroxy-4-methyl-2H-chromen-2-one (i) (7.66 g, 30 mmol), 4-(4-methylpiperazine-1-carbonyl)phenylboronic acid hydrochloride (2) (10.24 g, 36 mmol), Na3PO4(22.14 g, 135 mmol), ethoxyethanol (140 g) and water (14 g) was purged with Argon for five minutes in a 250 ml, pressure vessel. Ligand Sphos (obtained from Aldrich, Cat No. 638072) (739 mg, 1.8 mmol) and Pd(OAc)2(202 mg, 0.90 mmol) were added under an Argon atmosphere then the vessel was sealed and heated for 60 min in a 150 C. oil bath with strong stirring. This process was repeated once. Upon cooling, the reaction mixtures were filtered through a silica plug using CH2Cl2and MeOH wash. The unified solutions were evaporated to 100 mL slowly diluted with water (100 mL) and crystallized at 0 C. The product was filtered, washed with 50% MeOH (2×30 mL) and dried to afford 18.52 g (81%) of the title compound.

According to the analysis of related databases, 55977-10-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MANNKIND CORPORATION; ZENG, QINGPING; TORO, ANDRAS; PATTERSON, JOHN BRUCE; WADE, WARREN STANFIELD; ZUBOVICS, ZOLTAN; YANG, YUN; WU, ZHIPENG; (403 pag.)JP2015/214548; (2015); A;,
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Synthetic Route of 1013031-65-6, 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 1013031-65-6, name is (2,6-Dibromophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

A Teflon reaction tube was charged with (2,6-dibromophenyl)methanol (1.00 g, 3.76 mmol) and DCM (10 mL). The solution was cooled to 00 C and DAST (0.55 mL, 4.1 mmol) was added. Themixture was stirred for 10 mm, then NaHCO3 (saturated solution, 10 mL) was added. The aqueous layer was extracted with DCM and the combined organics dried (MgSO4) and concentrated. The residue was purified by column chromatography (Si02, 0-30% EtOAc/hex) to yield 1,3-dibromo-2- (fluoromethyl)benzene.

According to the analysis of related databases, 1013031-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; APPLEBY, Todd; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; GUERRERO, Juan A.; JABRI, Salman Y.; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; NOTTE, Gregory; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (724 pag.)WO2018/195321; (2018); 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.624-08-8, name is Heptadecan-9-ol, molecular formula is C17H36O, molecular weight is 256.4672, as common compound, the synthetic route is as follows.Computed Properties of C17H36O

9-Heptadecane p-Toluenesulfonate (3): p-toluenesulfonyl chloride (14.7 g, 77 mmol) in CH2Cl2 (60 mL) was added dropwise to a solution of heptadecan-9-ol (2) (18.00 g, 70 mmol) and triethylamine (Et3N) (24.4 mL, 181 mmol) in CH2Cl2 (90 mL) in a dry 250 mL flask. The mixture was stirred for 2 h, 250 mL of water was added, and the mixture was extracted three times with CH2Cl2 (3 * 150 mL). ;The organic phase was washed with water, dried (Na2SO4), and concentrated under reduced pressure. The crude product was purified by silica-gel flash chromatography (cyclohexane-ethyl acetate, 95-5 as eluent) to give 22.5 g of colorless oil, which crystallized as the title product (yield: 78%). 1H NMR (400 MHz, CDCl3): delta (ppm) 7.78 (d, J = 8.3 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H), 4.54 (p, J = 6.0 Hz, 1H), 2.43 (s, 3H), 1.55 (m, 4H), 1.21 (m, 24H), 0.88 (t, 6H). 13C NMR (101 MHz, CDCl3): delta (ppm) 144.38, 134.97, 129.74, 127.85, 84.78, 70.82, 34.26, 31.97, 29.48, 29.42, 29.28, 24.81, 22.78, 21.71, 14.23. FT-IR (ATR): nu = 2954, 2923, 2852, 1598, 1521, 1495, 1465, 1354, 1305, 1173, 1097, 1020, 895, 816, 766, 720, 662, 575, 554 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,624-08-8, Heptadecan-9-ol, and friends who are interested can also refer to it.

Reference:
Article; Garbay; Muccioli; Pavlopoulou; Hanifa; Hadziioannou; Brochon; Cloutet; Polymer; vol. 119; (2017); p. 274 – 284;,
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Electric Literature of 55357-38-5 ,Some common heterocyclic compound, 55357-38-5, molecular formula is C12H21NO4S, 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 solution comprising compound la prepared starting from 7.4 gr. of compound 2a a solution of 12.7 gr. of choline tosylate in dry acetonitrile was added. A solution of 5.9 ml. of triethylamine in 4 ml. DCM was added thereto. The reaction mixture was stirred overnight. The reaction mixture was then concentrated, 250 ml. of hexane was added and evaporated to dryness. The residue was redissolved in 390 ml. of THF and precipitated choline tosylate was filtered. Concentrated HCl (1. 7ml) was added and the reaction mixture was stirred for 1 hour. The reaction mixture was dried over magnesium sulfate, filtered, and the pH was basified with triethylamine. The precipitation was filtered, the filtrate was evaporated to dryness and then redissolved in a solvent mixture consisting of chloroform, methanol and water (8: 4: 3). The lower phase was separated and washed 4 times with the same upper phase and evaporated. The crude product was dissolved in 45 ml. of 1M tetrabutylammonium fluoride in THF and the reaction mixture was stirred at 45C for 2 hours. The resulting solution was evaporated and the crude product was purified by silicagel chromatographic column. (Eluent: gradual mounting concentration of methanol in chloroform). The relevant fractions were evaporated and the resulting product was then co-evaporated with acetonitrile. 1.49 of pure product was obtained (23% yield). 1H NMR 300 MHz (8 ppm, CD30D) : 0.92 (t, 3H), 1.31 (bm, 20H), 1.44 (m, 2H), 2.10 (q, 2H), 2.92 (m, 1H), 3. 33 (m, 1H), 3.67 (m, 2H), 3.92 (m, 1H), 4.04 (m, 2H), 4.30 (m, 2H), 5.55 (dd, 1H), 5. 78 (dt, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55357-38-5, its application will become more common.

Reference:
Patent; BIOLAB LTD.; WO2005/68480; (2005); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 813-99-0, name is 3-Chloro-2,2-bis(chloromethyl)propan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. category: alcohols-buliding-blocks

3-Chloro-2,2-bis (chloromethyl) propan-1-ol (15.4 g, 80.4 mmol) obtained in the above step 1 was dissolved in 98% ethanol (28 ml) and potassium hydroxide (5.0 g, mmol) was added, and the mixture was heated and refluxed for 30 minutes.The reaction solution was cooled with ice water and stirred for 10 minutes. The resulting solid was filtered off,The pH was adjusted to 7.5 with 2N aqueous hydrochloric acid solution. After removing the solvent by distillation under reduced pressure, water (100 ml) was added to the residue and extracted twice with ethyl acetate (150 ml). The obtained organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 4: 1) to obtain pure 3,3-bis (chloromethyl) oxetane (9.2 g, 74%).

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, 813-99-0, 3-Chloro-2,2-bis(chloromethyl)propan-1-ol.

Reference:
Patent; Korea Research Institute of Chemical Technology; Eseuti Pam Co., Ltd.; Kim Bong-jin; Kim Jae-hak; Lee Il-yeong; Lee Sang-ho; Lee Jong-gyo; Kim Gyeong-jin; Kim Uk-il; Nam Hwa-jeong; (56 pag.)KR101592370; (2016); B1;,
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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. 72995-94-9, name is 14-Bromotetradecan-1-ol, molecular formula is C14H29BrO, 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. COA of Formula: C14H29BrO

(5) A solution of n-butyl lithium (1.8 ml) was added dropwise to a 5 ml THF solution of 560 mg of 1,1-(ethylenedioxy)-4-methyl-3-(phenylsulfonyl)-cyclohexane and 4 mg of triphenylmethane under an argon stream at -78 C. The resulting mixture was stirred for 10 minutes and then reacted at room temperature for one hour. HMPT (1 ml) was added and the resulting mixture was cooled again to -78 C., followed by the dropwise addition of a 2 ml THF solution of 205 mg of 14-bromo-1-tetradecanol. After the reaction at -20 C. for 2 hours, the reaction mixture was poured into a saturated solution of ammonium chloride. The resulting mixture was extracted with diethyl ether. The organic layer was washed with water and saturated saline, dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column while using hexane-ethyl acetate, whereby 1,1-(ethylenedioxy)-3-(14-hydroxytetradecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane was obtained in the form of a colorless oil (yield: 98%).

With the rapid development of chemical substances, we look forward to future research findings about 72995-94-9.

Reference:
Patent; Luu, Bang; Mohier, Eliane; Yamada, Masashi; Suma, Yukie; Suzuki, Hiroto; US2004/115810; (2004); A1;,
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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. 81335-87-7, name is (2-Amino-4-methylphenyl)methanol. A new synthetic method of this compound is introduced below., Safety of (2-Amino-4-methylphenyl)methanol

General procedure: A solution of 4-toluene sulfonyl chloride (4.58 g, 1.2 equiv) or methanesulfonyl chloride (1.9 mL, 1.2 equiv) and pyridine (2 mL, 1.3 equiv) in 20 mL CH2Cl2 was added slowly to the solution of compound 11 (0.02 mol) in 40 mL CH2Cl2. The mixture was stirred overnight at room temperature. Then 30 mL diluted HCl solution was added to the reaction mixture, the organic layer was separated using separating funnel. Subequently, the aqueous phase was extracted with 15 mL CH2Cl2 three times, the combined organic layers were washed separately with saturated NaHCO3 (30 mL) and saturated NaCl (30 mL) three times. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography using petroleum ether/EtOAc = 1/1 to give the product 12.

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, 81335-87-7, (2-Amino-4-methylphenyl)methanol.

Reference:
Article; Xu, Changrui; Wu, Zhengxing; Chen, Jianzhong; Xie, Fang; Zhang, Wanbin; Tetrahedron; vol. 73; 14; (2017); p. 1904 – 1910;,
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Synthetic Route of 6214-45-5, 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.6214-45-5, name is (4-Butoxyphenyl)methanol, molecular formula is C11H16O2, molecular weight is 180.24, as common compound, the synthetic route is as follows.

Example 8 4-[(4-Butoxyphenyl)methyl]-1,2-dihydro-5-methyl-3 H -pyrazol-3-one The title compound was prepared in a similar manner to that described in Example 1 using 4-butoxybenzyl alcohol instead of 4-isopropoxybenzyl alcohol. 1H-NMR (500MHz, DMSO-d6) delta ppm: 0.91 (3H, t, J=7.4Hz), 1.30-1.50 (2H, m), 1.55-1.75 (2H, m), 1.98 (3H, s), 3.46 (2H, s), 3.80-3.95 (2H, m), 6.70-6.85 (2H, m), 6.95-7.10 (2H, m)

Statistics shows that 6214-45-5 is playing an increasingly important role. we look forward to future research findings about (4-Butoxyphenyl)methanol.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1213296; (2002); A1;,
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Related Products of 81335-87-7, 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 81335-87-7 as follows.

Sub-1 (35.0g, 255.1mmol), 3,5-dimethylacetophenone (56.7g, 382.7mmol), tris (triphenylphosphine) ruthenium (II) dichloride (2mol%) And potassium hydroxide (15.7g, 280.7mmol) and toluene (300mL) were added to the reaction flask,Heat and stir to reflux, and separate water by condensing reflux trap. When the reaction is over, drop to room temperature and filter on a pad of silica gel. The product was further purified by column (eluent: n-hexane / ethyl acetate = 2/100), and finally the intermediate Sub-3 (35.3 g, yield 56%) was obtained by crystallization from isopropanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,81335-87-7, its application will become more common.

Reference:
Patent; Zhejiang Huaxian Optoelectric Technology Co., Ltd.; Zheng Xianzhe; Zhao Xiaoyu; Hua Wanming; (31 pag.)CN110452271; (2019); A;,
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