Category: alcohols-buliding-blocks

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.623-04-1, name is (4-Aminophenyl)methanol, molecular formula is C7H9NO, molecular weight is 123.1525, as common compound, the synthetic route is as follows.Quality Control of (4-Aminophenyl)methanol

The specific process is: 4-aminobenzyl alcohol (1.48g, 12mmol) with 4N sulfuric acid (15mL) is dissolved, and cooled to 0 C. then sodium nitrite (1.66 g, 24 mmol) was dissolved in water (10 mL) and dissolved, and then added dropwise. after controlling the temperature at 0 C for 30 min. sodium azide (2.34 g, 36 mmol) was dissolved in water (10 mL), and added dropwise to the above reaction solution, and slowly warmed to room temperature for 1 h. After completion of the reaction, the mixture was extracted with ethyl acetate. The organic phase was combined, and the organic phase was washed with a saturated sodium chloride solution, and the organic phase was dried over anhydrous sodium sulfate. Purified with petroleum ether / 0-10% ethyl acetate)The product was obtained as a yellowish solid, 4-azidobenzyl alcohol, yield 90%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,623-04-1, (4-Aminophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Hezhou College; Zhu Dongjian; Ren Aishan; Cai Wen; Duan Zhenhua; (20 pag.)CN109134344; (2019); A;,
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Electric Literature of 104-38-1, 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.104-38-1, name is 1,4-Bis(2-hydroxyethoxy)benzene, molecular formula is C10H14O4, molecular weight is 198.2158, as common compound, the synthetic route is as follows.

Example 120 2-[4-(2-{[3-(1-Piperazinyl)-2-pyrazinyl]oxy}ethoxy)phenoxy]ethanol, Maleate The title product was prepared from 1,4-bis(2-hydroxyethoxy)benzene. Yield of free base of the title compound 51%. The maleate salt was prepared: mp 127-129 C. MS m/z 361 (M+H). Anal. (C18H24N4O4.C4H4O4) C, H, N.

The chemical industry reduces the impact on the environment during synthesis 104-38-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Biovitrum AB; US6465467; (2002); B1;,
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Application of 163119-16-2, 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. 163119-16-2, name is 2,6-Di-tert-butyl-4-methylcyclohexanol, molecular formula is C15H30O, 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.

To a mixture of 186 g of Compound (I-7) and 272 g of the foregoing Intermediate (I-6) suspended in 1.4 liter of ethyl acetate, 161 g of potassium acetate and 387 ml of anhydrous acetic acid were added in this order and stirred at 45 C. for 3 hours on a steam bath to react them. Thereafter, the reaction mixture was cooled on an ice bath and then 1 liter of water was added. Following stirring for 1 hour while cooling on an ice bath, precipitated crystals were collected by filtration. The crystals were washed with water. Crystals thus obtained were suspended in 1.5 liters of methanol and then 400 ml of a 25% aqueous ammonia was added. The resulting mixture was stirred at 40 C. for 3 hours on a hot water bath and then cooled on an ice bath and subjected to neutralization with dilute hydrochloric acid. Precipitated crystals were collected by filtration. The crystals were washed with water and dried. As a result, 291 g (yield 66%) of the objective Intermediate (I-8) was obtained, as a white crystal.

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 163119-16-2, 2,6-Di-tert-butyl-4-methylcyclohexanol.

Reference:
Patent; Fuji Photo Film Co., Ltd.; US6649771; (2003); B2;,
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Application of 25574-11-2, 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.25574-11-2, name is 3-(4-Bromophenyl)propan-1-ol, molecular formula is C9H11BrO, molecular weight is 215.087, as common compound, the synthetic route is as follows.

General procedure: An evacuated and argon purged 250 mLthree-necked round-bottom flask equipped with a Teflon-coated magnetic stirringbar, argon inlet, reflux condenser and gas bubbler was charged with30.0 mmol (1.0 eq) 4-bromoaryl derivative. It was dissolved in60 mL degassed EtOH:H2O = 7:3 (v/v) under argon and 3.90 g(60.0 mmol, 2.0 eq) NaN3, 297 mg (1.50 mmol, 5.0 mol %)sodiumascorbate, 571 mg (3.00 mmol, 10 mol%) as well as 485 muL (397 mg,4.50 mmol, 15 mol%) N,N?-dimethylethylenediamine(DMEDA) were added, respectively. The bluish suspension wasadditionally degassed for three times applying vacuum to the suspension untilthe solvent started to boil, which was immediately afterwards purged withargon. It was heated under reflux in an oil bath at 100 C for 2 huntil reaction control via GC-MSshowed quantitative conversion of the starting material. Subsequently, the bluishsuspension was cooled to room temperature and the solvent was removed on arotary evaporator. The residual, brownish solid was diluted with 300 mLEtOAc and the organic phase was washed with 1 M HCl (2 x 150 mL).Afterwards the product was re-extracted from the brownish, aqueous phase withEtOAc (1 x 50 mL), the combined brownish, organic phases were washed withhalf-saturated NaHCO3 (2 x 150 mL) and again re-extracted withEtOAc (1 x 50 mL). The combined yellowish, organic phases were dried overMgSO4, filtered, and concentrated on a rotary evaporator. Finally, the brownish, viscous liquid was purified via flash column chromatography(250 g SiO2, column: 22.0 x 6.0 cm) and the resultingyellowish liquid dried under high vacuum.

The chemical industry reduces the impact on the environment during synthesis 25574-11-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Leypold, Mario; Wallace, Paal W.; Kljajic, Marko; Schittmayer, Matthias; Pletz, Jakob; Illaszewicz-Trattner, Carina; Guebitz, Georg M.; Birner-Gruenberger, Ruth; Breinbauer, Rolf; Tetrahedron Letters; vol. 56; 41; (2015); p. 5619 – 5622;,
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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. 1072-52-2, name is 2-(Aziridin-1-yl)ethanol, molecular formula is C4H9NO, 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. name: 2-(Aziridin-1-yl)ethanol

(1) Preparation of 1-[2-(2-hydroxyethylamino)ethyl]-4-(4-nitrophenyl)piperazine (compound 75) In 20 ml of chloroform was dissolved 4 g of 1-(4-nitrophenyl)piperazine (compound 66) and 0.52 ml of 1-(2-hydroxyethyl)aziridine, and the solvent was distilled off from the resulting reaction mixture under reduced pressure. To the residue was added 10 mg of Amberlist 15 (trade name; made by Rohm & Haas Co.), and the mixture was then heated with stirring at 100 C. for 3 hour. Afterward, the temperature of the reaction mixture was returned to room temperature. To the reaction mixture was added 20 ml of chloroform, and insoluble matters were then removed therefrom by filtration. The filtrate was concentrated, and the resulting residue (concentrate) was purified through a silica gel column chromatograph (chloroform/methanol=100/1 to 25/1 in terms of volume ratio), thereby preparing 1 g of 1-[2-(2-hydroxyethylamino)ethyl]-4-(4-nitrophenyl)piperazine (compound 75).

With the rapid development of chemical substances, we look forward to future research findings about 1072-52-2.

Reference:
Patent; Mitsui Toatsu Chemicals, Incorporated; US5008267; (1991); A;,
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Reference of 29683-23-6, 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 29683-23-6, name is Tetrahydro-2H-thiopyran-4-ol. This compound has unique chemical properties. The synthetic route is as follows.

Compound was added 4.14 parts of 25 parts of chloroformrepresented by the formula (I-49-b), and stirred for 30 minutes at 23 C.. Tothe resulting mixed solution was added compound 6.82 parts of the formula(I-49-c), was further stirred for 1 hour at 23 C.. To the resulting reactionmass was stirred for 30 min at 23 C. was added 12.5 parts of ion-exchangedwater, the organic layer was removed by liquid separation. This operation wasrepeated seven times. By concentrating the obtained organic layer to give thecompound 6.12 parts of the formula (I-49-d)

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 29683-23-6, Tetrahydro-2H-thiopyran-4-ol.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; ANRYU, YUKAKO; ICHIKAWA, KOJI; (90 pag.)JP2015/27992; (2015); A;,
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Electric Literature of 2919-23-5, 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 2919-23-5, name is Cyclobutanol. This compound has unique chemical properties. The synthetic route is as follows.

[CAS Reg. No. 1822782-90-0] DIAD (1.22 mL, 6.20 mmol) was added to a mixture of isoquinolin-6-ol (600 mg, 4.13 mmol), cyclobutanol (0.324 mL, 4.13 mmol) and PPh3 (1.63 g, 6.20 mmol) in anhyd THF (5 mL) at r.t. for 16 h. Additional PPh3 (1.63 g, 6.20 mmol) and DIAD (1.22 mL, 6.20 mmol) were added and the suspension was stirred at r.t. for a further 5 h. The mixture was loaded onto an SCX column; the column was first eluted with MeOH to remove by-products, then with 7 N ammonia in MeOH. Fractions containing the desired product were evaporated onto silica gel. The crude product was purified by flash silica gel chromatography (eluent: gradient 0 to 10% MeOH in CH2Cl2). Fractions containing the desired product were combined and evaporated to dryness to afford the title compound 29 (800 mg, 97%) as a yellow oil. MS (ES+): m/z = 200 [M + H]+.

According to the analysis of related databases, 2919-23-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pearson, Stuart E.; Fillery, Shaun M.; Goldberg, Kristin; Demeritt, Julie E.; Eden, Jonathan; Finlayson, Jonathan; Patel, Anil; Synthesis; vol. 50; 24; (2018); p. 4963 – 4981;,
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Application of 2566-44-1, 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. 2566-44-1, name is 2-Cyclopropylethanol, molecular formula is C5H10O, 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.

The head space above a mixture of di-tert-butyl [(lr,4r)-6′-bromo-4-methoxy-5″-methyl-3’H- dispiro[cyclohexane-l,2′-indene-l’,2″-imidazol]-4″-yl]imidodicarbonate (Intermediate 9, 210 mg, 0.36 mmol), di-tert-butyl(2′,4′,6′-triisopropyl-3-methoxy-6-methylbiphenyl-2-yl)phosphine (10 mg, 0.02 mmol), allylpalladium chloride dimer (2.7 mg, 7.3 muiotaetaomicron), cesium carbonate (178 mg, 0.55 mmol) and 2-cyclopropylethanol (63 mg, 0.73 mmol) was evacuated and refilled with argon. Toluene (1.3 mL) was added and the mixture was heated at 90 C for 3 days. After another two days at r.t. the reaction mixture was filtered through a syringe filter. The filter was washed with 7 M ammonia in methanol (1.56 mL, 10.9 mmol). More 7 M ammonia in methanol (1.56 mL, 10.9 mmol) was added and the resulting solution was heated at 85 C for 24 h. After cooling to r.t. the mixture was concentrated. The residue was partitioned between EtOAc and 2 M aq. citric acid. The phases were separated and the organic layer was extracted twice with 2 M aq. citric acid. The organic layer was discarded. The aqueous citric acid phases were basified with NaOH (50% aq.) and extracted twice with EtOAc. The organic phase was treated with active charcoal, dried (Na2S0 ), filtered through diatomaceous earth and concentrated. Purification by flash silica gel chromatography, using a gradient of CHC^/MeOH (20: 1-15: 1-10: 1) gave the title compound (56 mg, 40% yield). 1H NMR (500 MHz, DMSO- ) delta ppm 0.02 – 0.12 (m, 2 H), 0.34 – 0.45 (m, 2 H), 0.72 – 0.84 (m, 1 H), 0.90 (td, 1 H), 1.07 – 1.27 (m, 2 H), 1.35 – 1.48 (m, 3 H), 1.53 (q, 2 H), 1.80 (d, 2 H), 2.15 (s, 3 H), 2.81 – 2.88 (m, 1 H), 2.88 – 2.98 (m, 2 H), 3.18 (s, 3 H), 3.80 – 3.91 (m, 2 H), 6.06 (d, 1 H), 6.50 (s, 2 H), 6.71 (dd, 1 H), 7.15 (d, 1 H); MS (ES+) m/z 382.1 [M+H]+.

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 2566-44-1, 2-Cyclopropylethanol.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; KARLSTROeM, Sofia; SOeDERMAN, Peter; SWAHN, Britt-Marie; Laszlo, Rakos; OeHBERG, Liselotte; WO2013/190301; (2013); A1;,
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Related Products of 3360-41-6, 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. 3360-41-6, name is 4-Phenylbutan-1-ol. A new synthetic method of this compound is introduced below.

Step 2 1-(4-(6-Bromohexyloxy)butyl)benzene: At 0~10 C., a solution of 4-phenylbutan-1-ol (8.4 g; 53.2 mmol; 1.00 equiv) in tetrahydrofuran (150 mL) was added to a suspension of sodium hydride (2.5 g; 62.5 mmol; 1.17 equiv) in tetrahydrofuran (50 mL). The resulting mixture was stirred at ambient temperature for about 1 hour and then 1,6-dibromohexane (41.0 g; 166 mmol; 3.13 equiv) and tetra-N-butylammonium bromide (100 mg; 0.27 mmol; 0.01 equiv) were added. The mixture was maintained at ambient temperature for about 16 hours, and then water was added. Following standard extractive workup with ethyl acetate, the crude residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1/8) to afford the title product as a yellow liquid (14.2 g; 84% yield). 1H NMR (300 MHz, CDCl3) delta: 7.30 (m, 2H), 7.15 (m, 3H), 3.43 (m, 6H), 2.66 (t, J=7.2, 7.5 Hz, 2H), 1.89 (m, 2H), 1.75~1.58 (m, 6H), 1.56~1.37 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3360-41-6, its application will become more common.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; US2010/9950; (2010); A1;,
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Reference of 702-82-9, 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. 702-82-9, name is 3-Aminoadamantan-1-ol. A new synthetic method of this compound is introduced below.

59.52 parts of a solution containing the salt represented by the formula (IV-1) and 3.81 parts of the compound represented by the formula (V-8)After stirring at 23 C. for 1 hour,It was filtered.The collected filtrate was concentrated,To the obtained concentrate,100 parts of chloroform and 30 parts of ion exchanged water were charged,After stirring for 30 minutes,And separated.This washing operation was repeated three times.By concentrating the recovered organic layer,9.44 parts of a salt represented by the formula (I-8) was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,702-82-9, 3-Aminoadamantan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Ichikawa, Koji; Sakamoto, Hiroshi; (89 pag.)JP5879696; (2016); B2;,
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