Category: alcohols-buliding-blocks

Electric Literature of 6971-51-3, 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. 6971-51-3, name is (3-Methoxyphenyl)methanol. A new synthetic method of this compound is introduced below.

General procedure: Geranyl bromide 12a was synthesized from geraniol via the reaction with PBr3.18 PBr3 (8.9 mmol) was added to cooled (0-5C) solution of geraniol (26.7 mmol) in dry ether (30 ml) and the reaction mixture was stirred for 2 h at r.t. Saturated aqueous NaHCO3 was added and the product was extracted with ether. The extracts were washed with brine, dried with Na2SO4 and evaporated. Other used bromides 12b-e were synthesized as described above. Compounds 12a, 12b, 12c and 12e (the yields 91%, 55%, 60% and 65%, respectively) were sufficiently pure and used for the next step without purification. The compound 12d was purified by column chromatography on SiO2, eluent – hexane (yield 24%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6971-51-3, (3-Methoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Khomenko, Tatyana M.; Zarubaev, Vladimir V.; Orshanskaya, Iana R.; Kadyrova, Renata A.; Sannikova, Victoria A.; Korchagina, Dina V.; Volcho, Konstantin P.; Salakhutdinov, Nariman F.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 13; (2017); p. 2920 – 2925;,
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Synthetic Route of 13674-16-3, 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 13674-16-3, name is Methyl 2-hydroxy-3-phenylpropanoate. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 194 (R)-2-[2-Bromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-6-methoxy-phenoxy]-3-phenyl-propionic acid Prepared from 2-bromo-4-(6-bromo-benzo [b]naphtho [2,3-d]thiophen-11-yl)-6-methoxy-phenol (Example 193) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96) according to the procedure in Example 113. White solid: mp >103 C. (dec.): NMR (CDCl3); delta8.36 (ddd, J=8, 1, 1 Hz, 1 H), 7.83 (ddd, J=8, 7, 1 Hz, 1 H), 7.67 (ddd, J=8, 7, 1 Hz, 1 H), 7.57-7.26 (m, 9 H), 7.18 (ddd, J=8, 7, 1 Hz, 1 H), 6.89 (ddd, J=8, 1, 1 Hz, 1H), 6.79 (ddd, J=8, 7, 1 Hz, 1H), 5.29 (t, 1H), 3.76, 3.74 (ds, 3 H), 3.39-3.46 (m, 2 H); MS (EI): [M+], 2 bromine isotope pattern, 660; Anal. Calc. for C32H22Br2O4S: C, 58.02, H, 3.35, N, 0.00. Found: C, 58.04, H, 3.73, N, 0.02.

According to the analysis of related databases, 13674-16-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; US6110962; (2000); A;,
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Application of 431-38-9 ,Some common heterocyclic compound, 431-38-9, molecular formula is C3H6F3NO, 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.

A solution of 150 mg intermediate 6-[4-(trifluoromethoxy)phenyl]-2-(3-fluorophenyl)-3-oxo-2,3- dihydropyridazine-4-carboxylic acid, 90.2 mg 3-amino-1 ,1 ,1 -trifluoro-2-propanol, 260.4 mg HATU, 0.18 mL ethyldiisopropylamine and 2 mg 4-dimethylaminopyridine in 2.5 mL of DMF was stirred at room temperature for 3 hours. Then the reaction mixture was filtered and subjected to RP-HPLC (Instrument: Labomatic HD-3000 HPLC gradient pump, Labomatic Labocol Vario-2000 fraction collector; column: Chromatorex C-18 125 mm x 30 mm, eluent A: 0.1 % formic acid in water, eluent B: acetonitrile; gradient: A 60% / B 40%? A 20% / B 80%; flow: 150 mL/min; UV-detection: 254 nm) to yield 101 mg 2-(3-fluorophenyl)-3-oxo-N-(3,3,3- trifluoro-2-hydroxypropyl)-6-[4-(trifluoromethoxy)phenyl]-2,3-dihydropyridazine-4-carboxamide. 1H NMR (400 MHz, DMSO-d6) delta ppm = 3.47 (ddd, 1 H), 3.70 – 3.81 (m, 1 H), 4.18 – 4.28 (m, 1 H), 6.66 (d, 1 H), 7.36 – 7.44 (m, 1 H), 7.51 (d, 2 H), 7.54 – 7.59 (m, 1 H), 7.59 – 7.67 (m, 2 H), 8.10 (d, 2 H), 8.69 (s, 1 H), 9.64 (t, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,431-38-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); SCHMEES, Norbert; GUTCHER, Ilona; IRLBACHER, Horst; BADER, Benjamin; ZHAO, Na; PLATTEN, Michael; (437 pag.)WO2017/202816; (2017); A1;,
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Reference of 14002-80-3, 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. 14002-80-3, name is Methyl 3-hydroxy-2,2-dimethylpropanoate, molecular formula is C6H12O3, 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.

Step A: methyl 3 -(5-bromopyridin-2-yloxyV2,2-dimethylpropanoateSodium hydride (60% disp. in oil, 908.0 mg, 22.7 mmol) was added portionwise at RT to a solution of 5-bromo~2-fiuoropyridine (1.16 mL, 11.4 mmol) and methyl 3-hydroxy-2,2- dimethylpropanoate (1.88 mL, 14.8 mmol) in anhydrous THF (33 mL) and dry 1 ,3 -dimethyl – 3,4,5,6-tetraliydro-2(lH)-pyrimidinone (5.0 mL) under argon. After 2 h of stirring at RT, the reaction mixture was heated at 50 C for 10 h and then at 70 C for 3 h. The suspension was cooled to RT and filtered over a thin celite pad. The celite pad was rinsed with Et20 (150 mL). The filtrate was concentrated to a volume of ca. 5 mL, then diluted with Et20 (150 mL), quenched with water (90 mL) and decanted. The aqueous layer was extracted with Et20; the combined organic extract was successively washed with water then brine, dried (MgSC^), filtered and concentrated. Purification by silica gel chromatography (eluant: 0-20%EtOAc hexanes) yielded the title compound as a clear oil. MS = 288, 290 [M+l).

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 14002-80-3, Methyl 3-hydroxy-2,2-dimethylpropanoate.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TING, Pauline, C.; ASLANIAN, Robert; CAO, Jianhua; KIM, David; ZORN, Nicolas; WO2012/24179; (2012); A1;,
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Application of 110-73-6, 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 110-73-6 as follows.

[0284] To the solution of compound of Example 1 (120 mg, 0.136 mmol) and catalytic amount of dimethylaminopyridine in CH2Cl2 (2 mL) at 0 C. was added pyridine (0.20 mL, 2.48 mmol) and diphosgen (0.08 mL, 0.66 mmol). The reaction was warmed to room temperature and stirred for 20 h. 2-(Ethylamino)ethanol (0.2 mL, 2.05 mmol) was added to the reaction and the mixture was stirred for another 16 h before being diluted with ethyl acetate (50 mL). The organic solution was washed with sat. aq. NH4Cl (5 mL¡Á2), sat. aq. NaHCO3 (5 mL) and brine, dried over MgSO4, and concentrated. The crude product was purified by chromatography (silica gel, 94:6:0.3 dichloromethane/methanol/conc. NH4OH). The purified product was dissolved in methanol (5 mL) and stirred at room temperature for 72 h. Concentration and purification by chromatography (silica gel, 92:8:0.3 dichloromethane/methanol/conc. NH4OH) yielded 17 mg (13%) of the title compound. MS 954 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,110-73-6, its application will become more common.

Reference:
Patent; Henninger, Todd C.; Macielag, Mark J.; Marinelli, Brett A.; Zhu, Bin; US2004/18994; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 61487-25-0, (2-Amino-3-chlorophenyl)methanol, 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: (2-Amino-3-chlorophenyl)methanol, blongs to alcohols-buliding-blocks compound. name: (2-Amino-3-chlorophenyl)methanol

Example 82 Preparation of 2-chloro-6-methoxymethylaniline A solution of 4.00 g (25.4 mmol) of 2-amino-3-chlorobenzyl alcohol in 30 ml of dry THF was cooled to -78C, treated with 16.7 ml (26.7 mmol) of 1.60 M n-butyllithium in hexane, warmed to 0-5C, treated with 3.61 g (25.4 mmol) of methyl iodide and heated at reflux for 5.5 hours. The solvent was removed by evaporation at reduced pressure. The residue was partitioned between 175 ml of ether and water, and the organic phase was separated and dried (MgSO4). The solvent was removed by evaporation at reduced pressure, and the residue was purified by HPLC eluding with EtoAc-hexane (5:95, v/v) to afford 1.1 g of the desired product as a pale brown oil. IR and 1H NMR spectra were in agreement with the assigned structure.

The synthetic route of 61487-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE DOW CHEMICAL COMPANY; EP142152; (1991); B1;,
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Related Products of 311-86-4 ,Some common heterocyclic compound, 311-86-4, molecular formula is C3H4BrF3O, 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.

733.2 mg of calcium hydroxide and 3343.3 mg of water were added to the reaction flask with the rectification apparatus.The mixture was heated to 90 C with stirring, and 1345 mg of 2-bromo-3,3,3-trifluoro-1-propanol was slowly added dropwise thereto for 1 h to obtain 1,1,1-trifluoro-2,3-epoxypropane. After chromatographic analysis, the yield was 74% and the selectivity was 100%, as shown in Figure 4.

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. 311-86-4, 2-Bromo-3,3,3-trifluoropropan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanxi Prolong Petroleum Group Fugui Chemical Co., Ltd.; Dalian Institute of Chemical Physics; Liu Jianguo; Deng Weiqiao; Yang Fengbin; Yin Shuangliang; Sun Tongrui; Meng Qingyu; Zhang Ling; Wu Haitao; (15 pag.)CN109369602; (2019); A;,
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Reference of 770-71-8, 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 770-71-8 as follows.

Example 1 Synthesis of (chloromethyl) (1-adamantylmethyl) ether represented by a structural formula: A Kjeldahl flask having a volume of 50 ml equipped with a nozzle for introducing hydrogen chloride gas was charged with 1.66 g (10 mmol) of 1-adamantylmethanol, 0.60 g (20 mmol) of paraformaldehyde, 1.20 g (10 mmol) of magnesium sulfate and 30 ml of dried dichloromethane, and it was cooled to 0C on an ice bath and stirred. Hydrogen chloride gas generated by mixing 10 g of sodium chloride with 50 ml of conc. sulfuric acid was blown thereinto through the nozzle for one hour. After further stirring for 60 minutes, magnesium sulfate was filtered, and then the solution was analyzed by gas chromatography to confirm that 1-adamantylmethanol was completely converted and that the intended product was obtained at a selectivity of 94.5 %. Hydrogen chloride and dichloromethane were removed, and then refining was carried out by distillation to isolate 1.87 g (8.72 mmol, yield 87.2 %) of the intended product. The analytical results of the above compound are shown below. ¡¤Nuclear magnetic resonance spectrometry (NMR): CDCl31H-NMR (500 MHz): 1.53 (6H, f), 1.64 to 1.72 (6H, d), 1.97 (3H, e), 3.25 (2H, b), 5.50 (2H, a),13C-NMR (126 MHz): 28.18 (e), 37.11 (d or f), 39.45 (d or f), 33.49 (c), 81.34 (b), 84.25 (a) ¡¤Infrared spectrometry (IR): 2905 cm-1 (C-H; str.), 1157 cm-1 (C-O-C; str.), 650 cm-1 (C-Cl; str.) ¡¤ Boiling point (bp): 130 to 133C/0.7 kPa

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,770-71-8, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN COMPANY LIMITED; EP1577285; (2005); A1;,
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Related Products of 92409-15-9, 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. 92409-15-9, name is 2-(2-Methoxyphenoxy)-1-(4-methoxyphenyl)propane-1,3-diol, molecular formula is C17H20O5, 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.

In 5 ml of quartz optical reaction tube, adding 0.05 mmol 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)-1,3-propanediol, 5 mg mpg-C3N4Catalyst, magneton, and add 1 ml solvent acetonitrile (substrate concentration is 0.05 mol/L). Air above the oxygen displacement reaction tube, and the opening is sealed, is arranged in the integrated light in the reaction device, the rotating speed of 500 r/min, the illumination wavelength is 405 nm (the power of 6 W), temperature constant at 40C, reaction 8 h. After the reaction, gas chromatography – mass spectrum detecting the product, and for high performance liquid chromatography quantitative, substrate conversion and product yield is shown in table 1.

According to the analysis of related databases, 92409-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dalian Institute of Chemical Physics; Wang Feng; Liu Huifang; Wang Min; Li Hongji; Luo Nengchao; Su Kaiyi; (14 pag.)CN109456160; (2019); A;,
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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.147034-01-3, name is (2,5-Dibromophenyl)methanol, molecular formula is C7H6Br2O, molecular weight is 265.93, as common compound, the synthetic route is as follows.Computed Properties of C7H6Br2O

To a stirred solution of (2,5-dibromo-phenyl)-methanol (45 g, 170 mmol) in THF (1000 mL) is added 60% NaH in mineral oil (10 g, 250 mmol) at 0 C. The mixture is stirred for 30 min and allyl bromide (25 g, 203 mmol) is added. Then the mixture is warmed up to room temperature for 12 hrs. The reaction is quenched with ice and the mixture is extracted with EtOAc. The organic layers are combined, dried and concentrated to give the crude product. Purification by flash column chromatography affords 45 g of 2-allyloxymethyl-l,4-dibromo-benzene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147034-01-3, (2,5-Dibromophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; COGAN, Derek; GUO, Xin; MARSHALL, Daniel Richard; MEYERS, Kenneth Michael; ZHANG, Yunlong; (130 pag.)WO2016/89800; (2016); A1;,
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