Category: alcohols-buliding-blocks

Electric Literature of 6850-39-1, 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 6850-39-1, name is 3-Aminocyclohexanol. This compound has unique chemical properties. The synthetic route is as follows.

Example 79 : N-IS-rO-hydroxycyclohexyDaminoin^^ltriazolon^-alpyridin-l- yl} nicotinamide (79); 3-amino-cyclohexanol (Betapharma, 67.33 mg; 0.58 mmol; 2.0 eq.) was added to a mixture of N-(5-chloro[l,2,4]triazolo[l,5-a]pyridin-2-yl)nicotinamide ((B4), 80 mg; 0.29 mmol; 1.0 eq.), DIEA (76 mg; 0.58 mmol; 2.0 eq.) and activated Charcoal (8 mg) in tBuOH (0.8 mL). The reaction mixture was heated at 2000C for 2 x 30 min under microwave irradiation. After this time, it was filtered on a celite pad and the cake was washed with ACN. The filtrate was directly purified by RP-HPLC (Starting with 15% ACN in water for 5 min, then up to 30% in 10 min.). The title compound was isolated after lyophilisation as a white powder (51 mg, 49%). HPLC, Rt: 2.14 min. (purity 98.0%). LC/MS, M+(ESI): 353.0, M (ESI): 351.0.

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 6850-39-1, 3-Aminocyclohexanol.

Reference:
Patent; LABORATOIRES SERONO SA; WO2009/27283; (2009); A1;,
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Synthetic Route of 624-95-3 , The common heterocyclic compound, 624-95-3, name is 3,3-Dimethylbutan-1-ol, molecular formula is C6H14O, 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.

16.9 g of 3, 3-Dimethyl-l-butanol (117.3 mmol) and 0.0765 g MeO-TEMPO (0. 411MMOL) are charged in a jacketed glass reaction flask as in Example I. Sodium borate (0.380 g, 1.0 mmol) and potassium bromide (0.011 g, 0.104 mmol) are dissolved in water (12.0 cc) and the aqueous solution is added to the stirred organic fraction at 1000 RPM in the reaction flask. The stirred suspension is cooled to 0C and the emulsion is re- adjusted to pH 8.4 using 50% solution of CH3COOH. When the temperature of the reactants reached 0C, 75.5 g (122 mmol) of 12. 1% aqueous NAOCI solution are pumped in via a gas-tight syringe over 90 minutes (The pH of the bleach solution was adjusted to 10 using 50% aqueous CH3COOH). During the bleach addition the pH was maintained at 8.3-8. 4 levels using a few drops of 50% aqueous CH3COOH. The reaction mixture is stirred for an additional 120 min at 0C and the organic layer is sampled for GC assay. The reaction in this second stage was kept at pH 8.4 by addition of 0.2-0. 25 cc aqueous solution OF NAOH (50% concentration). The yield of 3, 3-dimethylbutyraldehyde is 94.0% at 60 min and 95.0% at 90 min reaction time. This yield is equivalent to the yield of Example III in which no potassium bromide was used.

The synthetic route of 624-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE NUTRASWEET COMPANY; WO2004/67484; (2004); A2;,
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Synthetic Route of 928-51-8, 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. 928-51-8, name is 4-Chlorobutan-1-ol. A new synthetic method of this compound is introduced below.

4-Chlorobutan-l-ol 7-a (180 g, 1658 mmol, CAS 928-51-8) was added to sodium thiomethoxide (656 g, 1965 mmol, 21% solution in water) at 0-5C. After addition, the mixture was allowed to warm to 25C and stirred for 48 h. The mixture was extracted with CHCI3. The separated organic layer was dried over Na2C03, filtered and evaporated under vacuum. The residue was distilled to afford the alcohol 9-a as an oil (144.2 g, 72%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,928-51-8, 4-Chlorobutan-1-ol, and friends who are interested can also refer to it.

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; WO2012/80449; (2012); 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. 1202577-61-4, name is trans-(4-(Trifluoromethyl)cyclohexyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. category: alcohols-buliding-blocks

General procedure: PPh3 (30.75 g, 117.4 mmol) was added slowly to a 0 C solution of (trans-4- (trifluoromethyl)cyclohexyl)methanol (17.8 g, 97.8 mmol) and CBr4 (38.85 g, 117.4 mmol) in dry DCM (200 mL). The reaction was stirred at room temperature overnight and then concentrated. Hexane/EtOAc (9/1, 300 ml) was added and the mixture was stirred for 1 hour and then filtered. The filtrate was concentrated and distilled under vacuum to give trans- 1 – (bromomethyl)-4-(trifluoromethyl)cyclohexane. XH NMR (300 MHz, CDC13): delta 3.30-3.28 (d, 2H), 2.02-1.92 (m, 5H), 1.70-1.59 (m, 1H), 1.40-1.27 (m, 2H), 1.13-1.00 (m, 2H)

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, 1202577-61-4, trans-(4-(Trifluoromethyl)cyclohexyl)methanol.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHRISTOPHER, Matthew, P.; FRADERA LLINAS, Francesc Xavier; MACHACEK, Michelle; MARTINEZ, Michelle; REUTERSHAN, Michael Hale; SHIZUKA, Manami; SUN, Binyuan; THOMPSON, Christopher Francis; TROTTER, B. Wesley; VOSS, Matthew, E.; YANG, Liping; WO2014/123882; (2014); A1;,
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Electric Literature of 748805-85-8, 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. 748805-85-8, name is (2-Amino-5-fluorophenyl)methanol. A new synthetic method of this compound is introduced below.

14.5 g of potassium monoethyl malonate was added to 20 mL of 6 mol/L cold hydrochloric acid and then the mixture was extracted with diethyl ether. The extract was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and then 20 mL of acetonitrile, 1.9 g of magnesium chloride, and 4.1 g of triethylamine were added to the resulting residue under ice cooling. The mixture was stirred at room temperature for 4 hours to obtain a suspension. 15 mL of acetonitrile and 2.8 g of carbonyldiimidazole were added to 3.5 g of 3-methyl-2,4,5-trifluorobenzoic acid and the mixture was stirred at room temperature for 4 hours. The reaction solution was added to the aforementioned suspension at room temperature and the mixture was stirred at 80 C. for 3 hours. 100 mL of 1 mol/L hydrochloric acid was added and then the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography (n-hexane/ethyl acetate=200) to obtain 3.9 g of ethyl 2-(3-methyl-2,4,5-trifluoro)benzoylacetate. 3 mL of the acetic anhydride and 3 mL of ethyl orthoformate were added to the obtained compound and the mixture was stirred at 130 C. for 6 hours. The solvent was evaporated under reduced pressure. The residue was subjected to azeotropic distillation twice with toluene and the resulting residue was dissolved in dichloromethane to prepare a 1 mol/L solution for use in the following reaction. 29.7 mL of N,N-dimethylformamide and 29.7 mL of the dichloromethane solution of ethoxyacrylate prepared earlier were added to 4.19 g of 2-amino-5-fluorophenylmethanol and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and ethyl acetate was added to the residue. The mixture was washed with water. The organic layer was dried using anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The resulting residue was dispersed in hexane, collected by filtration, and dried under reduced pressure to obtain 10.4 g of the title compound. 1H-NMR (DMSO-d6): delta 0.91 (0.9H, t, J=7.1 Hz), 1.00 (2.1H, t, J=7.2 Hz), 2.21 (3H, brs), 3.97-4.03 (2H, m), 4.60 (2H, d, J=4.6 Hz), 5. 79-5.83 (1H, m), 7.20-7.29 (2H, m), 7.36-7.45 (1H, m), 7.58 (0.3H, dd, J=4.5, 8.6 Hz), 7.65 (0.7H, dd, J=4.8, 8.7 Hz), 8.36 (0.3H, d, J=14.3 Hz), 8.46 (0.7H, d, J=13.8 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,748805-85-8, its application will become more common.

Reference:
Patent; WAKUNAGA PHARMACEUTICAL CO., LTD.; KINOSHITA, Tomohiko; KURAMOTO, Yasuhiro; INOUE, Satoshi; NISHIMURA, Kouji; HIRANO, Tatsuya; ARAI, Mai; SAKURAI, Asuka; KAZAMORI, Daichi; SASAKI, Ayuka; (105 pag.)US2019/276407; (2019); A1;,
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Reference of 17100-58-2, Adding some certain compound to certain chemical reactions, such as: 17100-58-2, name is (4-Bromo-2-methylphenyl)methanol,molecular formula is C8H9BrO, 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 17100-58-2.

[00281] 28B. 4-bromo-2-methylbenzaldehyde: To a solution of oxalyl chloride (249 mL, 497 mmol) in CH2CI2 (150 mL) at -78 C under argon was added a solution of DMSO (42.4 mL, 597 mmol) in CH2C12 (75 mL) dropwise with a venting needle (Note: gas was generated, slow addition was necessary). After the addition, the venting needle was removed. The reaction mixture was stirred at -78 C under argon for 30 min. Then, a solution of 28A (20.0 g, 99.0 mmol) in CH2C12 (203 mL) was added. The resulting solution was stirred at -78 C for 30 min and then TEA (166 mL, 1190 mmol) was added dropwise. The reaction mixture was warmed to rt and stirred for 12 h. The reaction mixture was diluted with water (20 mL) and CH2C12 (30 mL). The layers were separated and the aqueous layer was extracted with CH2C12 (3 x 50 mL). The combined organic extracts were washed with water and brine, dried (MgSC^), filtered, and concentrated. The crude product was purified by flash chromatography to provide 28B (15.4 g, 78 mmol, 78 % yield) as a yellow oil. lH NMR (400 MHz, CDC13) delta 10.22 (s, 1H), 7.66 (d, J= 8.28 Hz, 1H), 7.51 (dd, J= 8.28, 1.76 Hz, 1H), 7.45 (s, 1H), 2.65 (s, 3H).

According to the analysis of related databases, 17100-58-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HERNANDEZ, Andres S.; ELLSWORTH, Bruce A.; EWING, William R.; CHEN, Bin; WO2014/78608; (2014); A1;,
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Reference of 33420-52-9, 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. 33420-52-9, name is 2,2-Difluoropropan-1-ol, molecular formula is C3H6F2O, 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.

7-[ 1 -(tert-butoxycarbonyl)piperidin-4-yl] -2-methyl-5-oxo-4,5-dihydropyrazolo[ 1 ,5-a]pyrimidine-3- carboxylic acid (100 mg, 266 muiotaetaomicron) was dissolved in tetrahydrofurane (5.0 ml, 62 mmol) and Nu,Nu’- Carbonyldiimidazole (86.2 mg, 531 muiotaetaomicron) was added. The mixture was heated at reflux for 1.5 h. Solvents were removed and 2,2-difluoropropan-l-ol (3.01 g, 31.4 mmol) was added. The mixture was heated at reflux for 18h and then purified by preparative HPLC (Method: column: Reprosil CI 8; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / solvents: A = water (0,01% formic acid), B = acetonitrile / gradient: 0.00-5.00 min = 10%B, 6.50min = 20%B, 17.0-19.75min = 100%B, 19.75.00-23.00min = 90%B). Evaporation of the combined product fractions yielded the title compound (105 mg, 99 % purity, 86 % of theory). LC-MS (Method 1 IB): Rt = 2.03 min; MS (ESIneg): m/z = 453 [M-H]

According to the analysis of related databases, 33420-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
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Reference of 7073-69-0, 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.7073-69-0, name is 2-(2-Bromophenyl)propan-2-ol, molecular formula is C9H11BrO, molecular weight is 215.087, as common compound, the synthetic route is as follows.

To the crude alcohol was added conc. HCl (3 drops) and 3,4-dihydro-2H-pyran (S3) (4.07 g, 48.5 mmol, 1.20 equiv) and stirred neat at room temperature for 24 h. The mixture was diluted with Et20 (50 mL), and washed with a sat. aq. NaHCO3 (25 mL). The aqueous layer was extracted with Et20 (2 x 50 mL) and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford 2-((2-(2-bromophenyl)propan-2-yl)oxy)tetrahydro-2H-pyran (S4) (8.30 g, ca. 38.8 mmol, 1.00 equiv) which was used without further purification.

Statistics shows that 7073-69-0 is playing an increasingly important role. we look forward to future research findings about 2-(2-Bromophenyl)propan-2-ol.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; HOYE, Adam, T.; KIM, Won-suk; MARTINEZ-SOLORIO, Dionicio; SMITH, Amos, B.; SANCHEZ, Luis; TONG, Rongbiao; NGUYEN, Minh, Huu; WO2013/185021; (2013); A2;,
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Synthetic Route of 52244-70-9, 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 52244-70-9, name is 4-(4-Methoxyphenyl)-1-butanol. This compound has unique chemical properties. The synthetic route is as follows.

Ammonia (75 ml) is liquified in a flask at -40° and a solution of 5 g (28 mmol) of p-(4-hydroxybutyl)-anisole in 25 ml ethanol is added 2.76 g (0.12 mmol) of sodium is added in small pieces over 1 h. The blue solution is then stirred at -40° for 10 min during which time the solution decolorizes with the formation of a white precipitate. The reaction is quenched using 5.88 g solid ammonium chloride followed by 25 ml water. The solvent is evaporated under a stream of nitrogen and then poured into brine and extracted with ether (4*100 ml). The organic extracts are combined, dried, filtered and subjected to evaporation to give 1-methoxy-4-(4-hydroxybutyl)-cyclohexa-1,4-diene as an oil.

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 52244-70-9, 4-(4-Methoxyphenyl)-1-butanol.

Reference:
Patent; Ciba-Geigy Corporation; US5153214; (1992); A;,
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Adding a certain compound to certain chemical reactions, such as: 33036-62-3, 4-Bromo-1-butanol, 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, 33036-62-3, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

PREPARATION 9 1-Tetrahydropyranyloxy-4-bromobutane (Formula XXIII: A is trimethylene) Concentrated hydrobromic acid (75 drops of 48%) is added with stirring to a mixture of 4-bromobutanol (150 ml.) and dihydropyran (300 ml.) at 0. This mixture is stirred and allowed to warm slowly to 25 C. during 15 hours. Evaporation under reduced pressure gives a residue which is divided into two equal parts, each part being chromatographed on 1.5 kg. of silica gel, each column being eluted with 7.5 l. of 5% ethyl acetate in Skellysolve B, and then with 4 l. of 7.5% ethyl acetate in Skellysolve B, collecting 500 ml. fractions. Fractions 5-11 from each column are evaporated to give a total of 240 g. of 1-tetrahydropyranyloxy-4-bromobutane.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33036-62-3, its application will become more common.

Reference:
Patent; The Upjohn Company; US3987083; (1976); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts