Category: alcohols-buliding-blocks

Synthetic Route of 15258-73-8, 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. 15258-73-8, name is (2,6-Dichlorophenyl)methanol, molecular formula is C7H6Cl2O, 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: To a solution of compound 8a (1.08 g, 10 mmol) and Et3N (1.52g, 15 mmol) in anhydrous DCM (100 mL) was added dropwisemethanesulfonyl chloride (1.36 g, 12 mmol) in anhydrous DCM(20 mL). The mixture was stirred for 12 h while being cooled withan ice-water bath. DCM was evaporated under vacuum. The residuewas dissolved in EtOAc (100 mL) and washed with 10% HCl(3 100 mL), saturated NaHCO3 (3 100 mL) and brine (3 100mL), and then dried over MgSO4 overnight. EtOAc was evaporatedto give 11a as yellow oil (1.77 g, yield: 95%). ESI-MS m/z 187.4 [M+H]+. The crude product was used directly in the next reactionwithout further purification.Compounds 11b-11w, 11aa-11ff and 23a-23h were preparedusing the same procedure described above.

According to the analysis of related databases, 15258-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cao, Jiangying; Ma, Chunhua; Zang, Jie; Gao, Shuai; Gao, Qianwen; Kong, Xiujie; Yan, Yugang; Liang, Xuewu; Ding, Qin’ge; Zhao, Chunlong; Wang, Binghe; Xu, Wenfang; Zhang, Yingjie; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3145 – 3157;,
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Related Products of 14320-38-8, 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 14320-38-8, name is Cyclopent-3-enol. This compound has unique chemical properties. The synthetic route is as follows.

Cyclopent-3-en-1-yl 4-methylbenzenesulfonate To a solution of cyclopent-3-ene-1-ol (70.2 g, 835 mmol) in pyridine (150 mL) and DCM (300 ml) cooled at 4 C. under N2 atm was added slowly with stirring 4-toluene-sulfonyl chloride (175 g, 918 mmol). The mixture was then stirred under N2 atm at this temperature for 1 h, then stood in cold room at 4 C. for 48 h. Most of the dichloromethane was evaporated at reduced pressure. The mixture was diluted with EtOAc/Hexane (20%, 600 ml) and washed with water (5*) and brine. The aqueous phases were back extracted with EtOAc/hexanes (20%, 1*400 ml), the organic layers combined, dried over MgSO4, and then filtered through a short plug (3 cm*11 cm) of silica (washed with a further 1000 ml 20% EtOAc/Hexane). The solvent was evaporated at reduced pressure to give a colorless oil. The residual solvent in the crude product was azeotroped with hexanes then twice with toluene. The resulting colorless oil was further dried by azeotroping once with hexanes and then crystallizing by diluting with an equal volume of hexane and heating at 50 C. The resulting biphasic mixture of colorless oil and solids in hexanes was allowed to age at RT overnight. The solid was removed by filtration and washed with cold hexanes and then dried in-vacuum to give the title compound (173 g, 727 mmol, 87%). 1H NMR (CHLOROFORM-d) delta: 7.79 (d, J=7.9 Hz, 2H), 7.34 (d, J=7.9 Hz, 2H), 5.65 (s, 2H), 5.11-5.24 (m, 1H), 2.59-2.67 (m, 2H), 2.48-2.55 (m, 2H), 2.45 (s, 3H).

According to the analysis of related databases, 14320-38-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Board of Regents, The University of Texas System; LEWIS, Richard T.; HAMILTON, Matthew; JONES, Philip; PETROCCHI, Alessia; REYNA, Naphtali; MCAFOOS, Timothy; CROSS, Jason Bryant; SOTH, Michael J.; US2020/24236; (2020); 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.7397-62-8, name is Butyl 2-hydroxyacetate, molecular formula is C6H12O3, molecular weight is 132.16, as common compound, the synthetic route is as follows.Recommanded Product: 7397-62-8

EXAMPLE 4 A suspension of 3-chloro-2-(2,4-difluoro-5-nitrophenyl)-4,5,6,7-tetrahydro-2H-indazole (10 g), butyl glycollate (5 g) and potassium fluoride (10 g) in dioxane (30 g) was refluxed for 1 hour. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. The residue was purified by liquid column chromatography using a mixture of hexane and ethyl acetate as an eluent to give 3-chloro-2-(2-fluoro-4-butyloxycarbonylmethoxy-5-nitro-phenyl)-4,5,6,7-tetrahydro-2H-indazole (10.2 g). m.p., 138-139 C. 1 H-NMR (delta, CDCl3): 0.92 (t, 3H, J=6 Hz), 1.1-2.1 (br, 8H), 2.1-2.9 (br, 4H), 4.2 (t, 2H, J=6 Hz), 4.8 (s, 2H), 6.82 (d, 1H, J=11 Hz), 8.03 (d, 1H, J=8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7397-62-8, Butyl 2-hydroxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4877444; (1989); A;,
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Application of 4442-79-9, Adding some certain compound to certain chemical reactions, such as: 4442-79-9, name is 2-Cyclohexylethanol,molecular formula is C8H16O, 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 4442-79-9.

A flame-dried 50 mL flask was charged with 2-cyclohexylethanol (1.00 equiv., 696 mg, 5.00 mmol) in dry THF (10 mL). The mixture was cooled at 0 C and sodium hydride (60 wt% on mineral oil, 1.50 equiv., 300 mg, 7.50 mmol) was added in one portion. After stirring for 10 min, allyl bromide (1.50 equiv., 0.65 mL, 7.50 mmol) was added dropwise at the same temperature. The cooling bath was removed and the suspension was stirred at r.t. for 30 min. The reaction mixture was then heated to reflux for 16 h. After full conversion, the suspension was cooled to r.t. and quenched by the addition of a saturated aqueous solution of NH4Cl (10 mL). The biphasic mixture was then extracted with Et2O (3 x 10 mL). The combined organic layers were dried over Na2SO4, and concentrated in vacuo. The crude material was purified by column chromatography on silica gel (Pet.Ether/EtOAc 100:1); Colorless oil; 87% yield; 1H NMR (200 MHz, CDCl3) delta: 5.98-5.73 (1H, m, =CH), 5.21 (1H, d, J = 17.2 Hz, =CHH), 5.10 (1H, d, J = 10.4 Hz, =CHH), 3.90 (2H, d, J = 4.0 Hz, OCH2), 3.40 (2H, t, J = 6.6 Hz, OCH2), 1.76-1.49 (5H, m, 2 x CH2 and CH), 1.49-1.33 (3H, m, 3 x CHH), 1.22-1.05 (3H, m, 3 x CHH), 0.73-0.69 (2H, m, 2x CHH); 13C NMR (50 MHz, CDCl3) delta: 135.0, 116.4, 71.7, 68.2, 37.1, 34.4, 33.3, 26.5, 26.2; MS 169 [M+H]+.

According to the analysis of related databases, 4442-79-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Voutyritsa, Errika; Nikitas, Nikolaos F.; Apostolopoulou, Mary K.; Gerogiannopoulou, Anna Dimitra D.; Kokotos, Christoforos G.; Synthesis; vol. 50; 17; (2018); p. 3395 – 3401;,
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Synthetic Route of 2043-47-2 ,Some common heterocyclic compound, 2043-47-2, molecular formula is C6H5F9O, 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.

18.8 g (71.1 mmol) of the fluorinated alcohol (Fluorochem Limited) and 8.63 g (85.3 mmol) of triethylamine are dissolved in 120 ml of dry toluene. 8.82 g (35.6 mmol) of 5- nitroisophthaloyl chloride is slowly added portionwise to the reaction mixture at 0-100C under nitrogen atmosphere. A large mass of a white solid is formed and as the reaction became difficult to stir, 280 ml of dry toluene is added. The reaction mixture is stirred at room temperature for 12 hours. Then water (300 ml) is added, the suspension is stirred for 1 hour and the solid is filtered off, washed repeatedly with water and dried in an oven to give14.9 g of the compound of formula 108, white solid, m.p. 91-92C. 1H NMR: (300 MHz, acetone-Gfe): delta = 9.00 (br s, ArH, 2H); 8.95 (br s, ArH, 1H); 4.83 (t, J = 6.0 Hz, OCH2CH2CF2, 4H); 3.05-2.80 (m, OCH2CH2CF2, 4H).

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. 2043-47-2, 1H,1H,2H,2H-Nonafluoro-1-hexanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CIBA SPECIALTY CHEMICALS HOLDING INC.; WO2006/82166; (2006); A1;,
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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 764-48-7, name is Ethylene Glycol Vinyl Ether. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Ethylene Glycol Vinyl Ether

C. General procedure for the Heck arylation ofhydroxyalkyl vinyl ethers (le-f)An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 2 (1.0 mmol), Pd(OAc)2 (0.025 mmol), DPPP (0.05 mmol), [HNEt3][BF4] (1.5 mmol), and [bmim] [BF4] (2 mL) under nitrogen at room temperature. Following degassing three times, a hydroxyalkyl vinyl ether 1 (2.0 mmol) and HN1Pr2 (1.5 mmol) were injected sequentially. The flask was placed in an oil bath, and the mixture was stirred and heated at 115 0C. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. A small sample was then taken for NMR analysis. The rest of the mixture was extracted with CH2Cl2 (3 x 20 mL), and the combined organic layer was washed with water until neutral, dried (Na2SO^, filtered, and concentrated in vacuo. The cyclic ketal derived from the arylated olefin was isolated out of the crude product by flash chromatography on silica gel using a mixture of ethyl acetate and hexane (10/90 to 20/80) containing 2% (in volume) triethylamine as eluant. The isolated yields of the products are given in Table 1.

With the rapid development of chemical substances, we look forward to future research findings about 764-48-7.

Reference:
Patent; THE UNIVERSITY OF LIVERPOOL; WO2007/57658; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 623-61-0, Isopropyl glycolate, 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, name: Isopropyl glycolate, blongs to alcohols-buliding-blocks compound. name: Isopropyl glycolate

General procedure: The nucleoside (3.21 mmol) was suspended in THF (25 ml). Under nitrogen and at 0 C., POCl3 (4.82 mmol) was added and the reaction mixture was allowed to reach at room temperature overnight. The reaction mixture was cooled down to 0 C. and a mixture of alcohol (3.53 mmol) and TEA (16.06 mmol) in CH3CN (10 ml) was added dropwise. The mixture was stirred at 0 C. during 1 hour. N-Methylimidazole (19.27 mmol) was added at 0 C. and after 15 min at 0 C., the reaction mixture was stirred at room temperature during 2 hours. The mixture was quenched on a solution 0.5M phosphate buffer (pH=7) and the product was extracted with CH2Cl2. The organic layer was dried on Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by silica gel chromatography (eluent: CH2Cl2/CH3CH2OH 0 to 20%) and by preparative MS/HPLC to give the expected compounds as a mixture of diastereoisomers. White solid; 1H NMR (DMSO-d6, 400 MHz) delta (ppm) 0.95 (s, 3H), 1.21-1.23 (m, 6H), 3.95 (s, 3H), 4.22-4.29 (m, 0.7H), 4.46-4.53 (m, 0.3H), 4.63-4.75 (m, 4H), 4.96-5.03 (m, 1H), 5.93 (brs, 1H), 6.07 (brs, 0.3H), 6.14 (brs, 0.7H), 6.48 (brs, 1H), 6.59 (s, 1H), 8.05 (s, 0.7H), 8.12 (brs, 0.3H); 31P NMR (DMSO-d6, 162 MHz) delta (ppm)-5.84 (s, 0.68P), -5.01 (s, 0.32P); MS (ESI) m/z=474.2 (MH+).

The synthetic route of 623-61-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PARSY, Christophe Claude; ALEXANDRE, Francois-Rene; DOUSSON, Cyril B.; DUKHAN, David; GOSSELIN, Gilles; RAHALI, Houcine; SURLERAUX, Dominique; US2013/315867; (2013); 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. 3236-48-4, name is trans-1,4-Cyclohexanedimethanol, molecular formula is C8H16O2, 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. Recommanded Product: 3236-48-4

Step D: Preparation of ((lr,4r)-4-(Hydroxymethyl)cyclohexyl)methyl-3- fluorophenyl(phenyl)carbamate.; A suspension of 4-(dimethylamino)- 1 -((3 -fluorophenyl)(phenyl)carbamoyl)-pyridinium chloride (88.25 g, 237 mmol), (lr,4r)-cyclohexane-l,4-diyldimethanol (137 g, 950 mmol) and 4-dimethylaminopyridine (29.0 g, 237 mmol) in acetonitrile (1 L) was heated at 53 0C for 18 h. Upon cooling, the solvent was removed, and the residue was taken up in isopropyl acetate (500 mL) and 1 N HCl (500 mL), heated to suspend all solids, and then filtered through glass fiber filter paper to remove the insoluble bis-carbamate impurity. The aqueous filtrate was discarded, and the organic filtrate was washed with an additional 500 mL of 1 N HCl, followed by water (5 x 500 mL). Heptane (100 mL) was added to the organic phase, which was further washed with water (2 x 500 mL) and brine (100 mL), dried over MgSO4, and concentrated to dryness. The residue was taken up in isopropyl acetate (100 mL) and heptane (300 mL) was added. Crystals gradually formed over 1 h, forming a white precipitate, which was collected by filtration, rinsing with 25percent isopropyl acetate/heptane (100 mL). The filtrate was concentrated to dryness, and the hot residue was taken up in 25percent isopropyl acetate/heptane (100 mL) and filtered hot. As the filtrate cooled, more solids precipitated, which were collected by filtration and combined with the first crop. This material still contained about 5percent bis-carbamate by-product, which could not be readily removed by filtration. The solid was then taken up in dichloromethane (200 mL) and subjected to plug filtration over 1.6 kg of silica gel, eluting the remaining bis-carbamate with dichloromethane and the product with 20percent ethyl acetate/dichloromethane to provide the title compound as a white solid (71 g). LCMS m/z = 358.2 [M+H]+; 1H NMR (CDCl3, 400 MHz) delta 0.91-0.98 (m, 4H), 1.35-1.44 (m, IH), 1.54-1.60 (m, IH), 1.68-1.73 (m, 2H), 1.79-1.83 (m, 2H), 3.45 (d, 7= 6.4 Hz, 2H), 4.01 (d, J= 6.4 Hz, 2H), 6.91 (t, J= 7.6 Hz, IH), 7.04 (d, J = 8.6 Hz, 2H), 7.22-7.30 (m, 4H), 7.38 (t, J = 7.8 Hz, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 3236-48-4.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
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Electric Literature of 3637-61-4, 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.3637-61-4, name is Cyclopentanemethanol, molecular formula is C6H12O, molecular weight is 100.16, as common compound, the synthetic route is as follows.

General procedure: Ionic liquid [Dsim]HSO4 (6.5 mg, ?0.02 mmol) was added to a stirred mixture of alcohol, phenol or naphthol (1.0 mmol) and HMDS (80 mg, 0.5 mmol) at room temperature under solvent free conditions. After completion of the reaction (monitored by TLC, It should be noted that when addition of HMDS is finished stirring of the mixture is stopped after 1 min. TLC showed that in most of the cases the reaction is completed immediately after the addition of HMDS), the product was extracted with Et2O and the ionic liquid was recovered and was dried at 65 ?C under vacuum to remove moisture, and then reused. Evaporation of the solvent under reduced pressure gave the highly pure product without further purification. The desired pure products were characterized by comparison of their IR, NMR and MS data as well as boiling poin twith those of known compounds

The chemical industry reduces the impact on the environment during synthesis 3637-61-4, I believe this compound will play a more active role in future production and life.

Reference:
Article; Shirini, Farhad; Khaligh, Nader Ghaffari; Akbari-Dadamahaleh, Somayeh; Journal of Molecular Catalysis A: Chemical; vol. 365; (2012); p. 15 – 23;,
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Related Products of 2807-30-9, 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. 2807-30-9, name is 2-Propoxyethanol. A new synthetic method of this compound is introduced below.

General procedure: p-Toluensulfonyl chloride (2.6 g, 0.014 mol) was slowly added to the mixture of appropriate2-alkoxyethanol respectively (oxiran-2-yl)methanol (0.014 mol) and triethylamine (1.84 g, 0.018 mol) indichlormethane (20 mL) cooled at 0 C. The mixture was then stirred for 1 h at ambient temperature.The precipitate was filtered and the organic phase was washed with 2 M HCl, saturated solutionof Na2CO3 and water, dried over MgSO4, and then the solvent was evaporated. Product T2 wasrecrystallized from petroleum ether/diethyl ether in ratio 5:1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2807-30-9, its application will become more common.

Reference:
Article; Marvanova, Pavlina; Padrtova, Tereza; Odehnalova, Klara; Hosik, Ondrej; Oravec, Michal; Mokry, Petr; Molecules; vol. 21; 12; (2016);,
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