Category: alcohols-buliding-blocks

Application of 349-75-7, 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 349-75-7 as follows.

Aniline (46.5 mg, 0.5 mmol),Cat.[Ir] (5.4 mg, 0.005 mmol, 1 mol%), cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.),3-trifluoromethylbenzyl alcohol (105.6 mg, 0.6 mmol) and t-amyl alcohol (1 ml) were sequentially added to 5 mLIn a round bottom flask.The reaction mixture was refluxed in air for 12 hours and then cooled to room temperature.The solvent was removed by rotary evaporation, followed by column chromatography (developer: petroleum ether/ethyl acetate) to give the pure target compound. Yield: 86%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,349-75-7, its application will become more common.

Reference:
Patent; Nanjing University of Science and Technology; Fan Hongjun; Li Shun; Liu Pengcheng; Li Feng; (9 pag.)CN107778182; (2018); A;,
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Electric Literature of 41175-50-2, 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 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol. This compound has unique chemical properties. The synthetic route is as follows.

8-Hydroxyjulolidine (1.4 g, 7.2 mmol) and 3-formyl benzoic acid (500 mg, 3.6 mmol) are mixed with 60% aqueous sulfuric (40 mE) and stirred at 150 C. for 24 hours under air atmosphere. The reactionmixture is addedto ice (100 g), after which 60% NaOH is careffilly added to pH 6-7, precipitating the crude product. The crude product is extracted between DCM and watet The organic phase is separated, and washed with brine. The organic solvent is removed and the final products are dried by evaporating with EtOH and toluene 5 times to yield 1.7 g 3-acid product (94% yield). Purity as determined by HPEC is 95%. MS (ESI) [M+]=491.

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 41175-50-2, 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol.

Reference:
Patent; Pharmacophotonics, Inc.; Bremberg, Ulf; Ringberg, Erik; Berts, Wei; De Belder, Anthony; Strickland, James S.; US9169398; (2015); B2;,
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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. 5333-42-6, name is 2-octyldodecan-1-ol, molecular formula is C20H42O, 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. Computed Properties of C20H42O

A 500-mL three-necked flask equipped with magnetic stirrer, septum, and thermometer was filled with argon. Triphenylphosphine (33.4 g, 0.127 mol, 1 equiv.) and 200 mL of anhydrous dichloromethane were placed into the flask. The solution was cooled to 0C, and 6.52 mL (20.34 g, 0.127 mol, 1 equiv.) of bromine was added dropwise so that the temperature of the reaction mix- ture was not higher 5C. After bromine addition was completed, the reaction mixture was stirred for 15 min at 0C, 45.36 mL (38.0 g, 0.127 mol, 1 equiv.) of2-octyl-1-dodecanol was added. The reaction mixture was stirred for 12 h at ambient temperature, concen- trated in a vacuum, the resultant suspension was diluted with 100 mL of petroleum ether, and filtered. The filtrate was passed through a thin layer of silica gel, washed with petroleum ether, and concentrated in a vacuum to give 43.61 g (95%) of viscous oil.1H NMR (400 MHz, CDCl3, delta, ppm): 3.47 (d, J =4.7 Hz, 2H), 1.66-1.54 (m, 1H), 1.45-1.17 (m, 32H),0.91 (t, J = 6.7 Hz, 6H).13C NMR (101 MHz, CDCl3, delta, ppm): 39.7, 39.5,32.5, 31.9, 29.8, 29.6, 29.6, 29.5, 29.3, 29.3, 26.5,22.6, 14.1.

With the rapid development of chemical substances, we look forward to future research findings about 5333-42-6.

Reference:
Article; Keshtov; Osipov; Topchiy; Zotova; Konstantinov; Krayushkin; Kuklin; Khokhlov; Doklady Chemistry; vol. 463; 2; (2015); p. 215 – 220; Dokl. Akad. Nauk; vol. 463; 6; (2015); p. 669 – 674,6;,
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Electric Literature of 115652-52-3, 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 115652-52-3 as follows.

Example 1Synthesis of: (/?)-3-((/?)-2-amino-3-(l-(hvdroxymethyl)cvclopropylamino)-3-oxopropylthio) propane- 1,2-diyl didodecanoateStep 1: (R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(l-(hydroxymethyl)cyclo- propylamino)-3-oxopropylthio)propane-l,2-diyl didodecanoate[000398] To a solution of (5«,9«)-9-(dodecanoyloxy)-l-(9H-fluoren-9-yl)-3,12-dioxo-2,l l- dioxa-7-thia-4-azatricosane-5-carboxylic acid (6, 1 eq) and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (3.5 eq), followed by (1-aminocyclopropyl) methanol hydrochloride (1.2 eq). The reaction was stirred at room temperature for 2 hours. The crude mixture was purified by flash chromatography on a COMBIFLASH system (ISCO) using 30-50% EtO Ac/Hex to give (R)-3- ((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(l-(hydroxymethyl)cyclopropylamino)-3- oxopropylthio)propane- 1 ,2-diyl didodecanoate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115652-52-3, its application will become more common.

Reference:
Patent; IRM LLC; WU, Tom Yao-Hsiang; ZOU, Yefen; HOFFMAN, Timothy Z.; PAN, Jianfeng; WO2011/119759; (2011); A1;,
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Related Products of 67853-03-6 ,Some common heterocyclic compound, 67853-03-6, molecular formula is C9H10O3, 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 stirred solution of methyl 3-(hydroxymethyl)benzoate (1.31 g, 7.88 mmol) in THF (10 mL) at RT, was added Cs2CO3 (3.8 g, 11.7 mmol) and the mixture stirred for 20 mm. To this was added a solution of 6-chloropyrimidine-4-carbonitrile B-i (750 mg, 7.17 mmol) in THF (15 mL) and the mixture stirred at RT for 16 h. The mixture was partitioned between water (100 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was re-extracted with EtOAc (20 ml). The combined organic layers were dried (MgSO4), filtered, and then concentrated under reduced pressure. The crude residue was purified (silica gel; eluting with 0- 60% EtOAc in hexanes), to afford compound B-2 as an off-white solid (1.01 g, 52%). ?H NMR (300 MHz, DMSO-d6): 8.97 (m, 1H), 8.06 (m, 1H), 7.94 (m, 1H), 7.82 (m, 1H), 7.75 (m, 1H), 7.56 (m, 1H), 5.56 (s, 2H), 3.84 (s, 3H); LCMS Mass: 270.0 (M+1).

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. 67853-03-6, Methyl 3-(hydroxymethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
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Electric Literature of 111-90-0, 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.

[00121] Charge copper (I) iodide (FW 190.45, 0.90 grams, 4.72 mmol), 1,10-phenanthroline (FW 180.21, 0.83 grams, 4.62 mmol), cesium carbonate (FW 325.82, 19.00 grams, 58.30 mmol), 1 ,3-diiodobenzene (FW 329.90, 7.50 grams, 22.70 mmol), di(ethylene glycol) ethyl ether (FW 134.71, 14.06 grams, 104.40 mmol) and 100 milliliters of dry xylene in a 350 milliliter three necked round bottom flask. The reaction mixture was heated with stirring at reflex temperature for 20 hours under nitrogen. The resulting suspension was cooled to room temperature by adding 50 milliliters of toluene. Then the reaction mixture was filtered through celite and alumina. The low boiling (xylene and toluene) component was removed by a rotary evaporator and high boiling component di(ethylene glycol) ethyl ether by air bath oven at 180C under high vacuum for 2 hours. The residue was purified by flask chromatography on silica gel. The final dark yellow product was yielded 5.20 grams (67%). The product IR, and C NMR analysis shows the formation of aryl ether product. IR: neat (cm” FontWeight=”Bold” FontSize=”10″ ): 687, 763, 843, 995, 1058, 1 116, 1 157, 1 185, 1264, 1289, 1333, 1351, 1418, 1452, 1492, 1590, 2874. 13C NM (CDC13): 149.22, 121.87, 1 15.18, 70.84, 70.65, 69.83, 68.90, 66.5, 15.12.

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; EXXONMOBIL RESEARCH AND ENGINEERING COMPANY; PATIL, Abhimanyu O.; BODIGE, Satish; WO2015/60984; (2015); A1;,
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Application of 29683-23-6 ,Some common heterocyclic compound, 29683-23-6, molecular formula is C5H10OS, 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.

INTERMEDIATE 17(2-Oxo-3 -tetrahydro-2H-thiopyran-4-yl-2,3 -dihydro- 1 H-benzimidazol- 1 -yPacetic acidStep A. fert-Butyl 2-oxo-3 -tetrahydro-2H-thiopyran-4-yl-2,3 -dihydro- 1 H-benzimidazole- 1 – carboxylateDiethyl azodicarboxylate (446 mg, 2.56 mmol) was added to a solution otert- butyl 2-oxo-2,3-dihydro-lH-benzimidazole-l -carboxylate (J Org. Chem., 1995, 60, 1565-1582) (500 mg, 2.13 mmol), triphenylphosphine (672 mg, 2.56 mmol), and tetrahydro-2H-thiopyran-4- ol (Chem. Comm., 2002, 10, 1070-1071) (303 mg, 2.56 mmol) in TetaF (10 mL). After 20 h, the reaction was concentrated in vacuo and the crude product purified by silica gel column chromatography, eluting with a gradient of hexane:EtOAc – 100:0 to 95:5, to give the title compound. MS: m/z = 335 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29683-23-6, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2008/130512; (2008); A1;,
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Electric Literature of 25125-21-7, 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.25125-21-7, name is 1-Hydroxymethyl-3-cyclopentene, molecular formula is C6H10O, molecular weight is 98.143, as common compound, the synthetic route is as follows.

1-a (Cyclopent-3-en-1-yl)methyl toluenesulfonate A mixture of (cyclopent-3-en-1-yl)methanol (1.96 g, 20 mmol) and para-toluenesulfonylchloride (3.81 g, 20 mmol) were stirred at room temperature for 2 hrs in pyridine (30 ml). After the concentration of pyridine, the reaction residues were extracted with dichloromethane, washed 1N HCl, dried with MgSO4, concentrated and separated by the column chromatography to give the desirable product (4.20 g). Yield(%): 83.2 1 H NMR(CDCl3): delta2.11(2H,m), 2.42(3H,s), 2.49(3H,m), 3.82(2H,d), 5.67(2H,s), 7.40(2H,d), 7.65(2H,d).

The chemical industry reduces the impact on the environment during synthesis 25125-21-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Samjin Pharmaceutical Co., Ltd; US5922727; (1999); A;,
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Adding a certain compound to certain chemical reactions, such as: 2516-33-8, Cyclopropylmethanol, 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, Safety of Cyclopropylmethanol, blongs to alcohols-buliding-blocks compound. Safety of Cyclopropylmethanol

To a 2 L flask was charged with cyclopropanemethanol (8A) (18 g, 250 mmol, 1 equiv), TEMPO (78 mg, 0.5 mmol) and CH2Cl2 (250 mL). The solution was cooled to 0 C, and a solution of KBr (2.99 g, 25 mmol, 0.1 equiv), NaHCO3 (52.5 g, 625 mmol, 2.5 equiv), and 10-13% NaOCl (150 mL, 313 mmol, 1.25 equiv) in H2O (80 mL) was then slowly added. After the resulting mixture was had been stirring at 0 C for 45 min, the two layers were separated. The aqueous layer was back extracted with CH2Cl2 (2 x 250 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resulting residue was purified via shortpath distillation head under N2 (95-100 C) to give the corresponding aldehyde 8B (11. 02 g, 73%) as a colorless liquid.

The synthetic route of 2516-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Trost, Barry M.; Nguyen, Hien M.; Koradin, Christopher; Tetrahedron Letters; vol. 52; 17; (2011); p. 2033 – 2036;,
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Synthetic Route of 20712-12-3, 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. 20712-12-3, name is (2-Amino-5-bromophenyl)methanol. A new synthetic method of this compound is introduced below.

A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20712-12-3, (2-Amino-5-bromophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Bifulco, JR., Neil; DiPietro, Lucian V.; Miduturu, Chandrasekhar V.; US2015/197519; (2015); A1;,
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