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Beta-alkoxy alcohol compound synthesis method

The technology of an alkoxy alcohol and a synthesis method is applied in the field of organic synthesis of organic intermediates, can solve the problems of high high temperature and high pressure risk factor, high yield of target compounds and high production cost, and achieves short reaction time, low production cost and high yield. rate increase effect

Inactive Publication Date: 2013-10-02
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] In order to overcome the deficiencies such as high production cost, serious pollution, use of toxic solvents or catalysts, high temperature and high pressure risk factor, and low yield in the prior art, the invention provides a catalyst with high catalytic activity (C 4 h 12 N 2 ) 2 [BiCl 6 ]Cl H 2 The synthesis method of β-alkoxy alcohols under O catalysis has a simple process, the catalyst can be recycled and used repeatedly, the regioselectivity is good, the yield of the target compound is high, the solvent-free reaction avoids the use of toxic solvents, and the industrial production has broad prospects

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1: the synthesis of 1-phenoxy-2-propanol (1), the synthetic route is:

[0032]

[0033] Add propylene oxide (0.012mol, 0.696g, analytically pure, Shanghai Jingchun Chemical Reagent Co., Ltd.), phenol (0.01mol, 0.94g, analytically pure, Shanghai Jingchun Chemical Reagent Co., Ltd.) and pre-prepared (C 4 h 12 N 2 ) 2 [BiCl 6 ]Cl H 2 O (0.0001mol, 0.05g), stirred and reacted at room temperature for 30min, then filtered, washed and dried to recover the catalyst, and the filtrate was added with 20mlH 2 Diluted with O, then extracted 3 times with 60ml ethyl acetate (analytical grade, Sinopharm Reagent), and the organic phase was sequentially washed with 20ml saturated NaHCO 3 solution, 20mlH 2 O, 20ml saturated NaCl solution washing, anhydrous NaCl 2 SO 4 Dry, remove ethyl acetate, and then separate by column chromatography (EA:PE=1:9 / 1:8 / 1:7 / 1:6) to obtain 1.40 g of the main product A.

[0034] 1-phenoxy-2-propanol: yield 92.1%, 1 H NMR(CDCl3)δ7.22-7...

Embodiment 2

[0035] Embodiment 2: Synthesis of 1-chloro-3-(4-methylphenoxy)-2-propanol (2), the synthetic route is:

[0036]

[0037] Add epichlorohydrin (0.012mol, 1.11g, analytically pure, Shanghai Jingchun Chemical Reagent Co., Ltd.), 4-methylphenol (0.01mol, 1.08g, analytically pure, Shanghai Jingchun Chemical Co., Ltd.) in a 25ml single-necked flask successively. Reagent Co., Ltd.) and pre-prepared (C 4 h12 N 2 ) 2 [BiCl 6 ]Cl H 2 O (0.0001mol, 0.05g), stirred and reacted at room temperature for 40min, then filtered, washed and dried to recover the catalyst, and the filtrate was added with 20mlH 2 Diluted with O, then extracted 3 times with 60ml ethyl acetate (analytical grade, Sinopharm Reagent), and the organic phase was sequentially washed with 20ml saturated NaHCO 3 solution, 20mlH 2 O, 20ml saturated NaCl solution washing, anhydrous NaCl 2 SO 4 Drying, removal of ethyl acetate, followed by column chromatography (EA:PE=1:9 / 1:8 / 1:7 / 1:6) afforded 1.80 g of a single produc...

Embodiment 3

[0039] Embodiment 3: Synthesis of 1-chloro-3-(1-naphthyloxy)-2-propanol (3), the synthetic route is:

[0040]

[0041] In a 25ml single-necked flask, add epichlorohydrin (0.012mol, 1.11g, analytically pure, Shanghai Jingchun Chemical Reagent Co., Ltd.), naphthol (0.01mol, 1.44g, analytically pure, Shanghai Jingchun Chemical Reagent Co., Ltd.) ) and pre-prepared (C 4 h 12 N 2 ) 2 [BiCl 6 ]Cl H 2 O (0.0001mol, 0.05g), stirred and reacted at room temperature for 50min, then filtered, washed and dried to recover the catalyst, and the filtrate was added with 20mlH 2 Diluted with O, then extracted 3 times with 60ml ethyl acetate (analytical grade, Sinopharm Reagent), and the organic phase was sequentially washed with 20ml saturated NaHCO 3 solution, 20mlH 2 O, 20ml saturated NaCl solution washing, anhydrous NaCl 2 SO 4 Drying, removal of ethyl acetate, followed by column chromatography (EA:PE=1:9 / 1:8 / 1:7 / 1:6) yielded 2.10 g of a single product C.

[0042] 1-chloro-3-(1-...

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Abstract

The invention discloses a beta-alkoxy alcohol compound synthesis method, which is characterized in that a mono-substituted epoxy compound or epoxy cyclohexane is adopted as a raw material, and reacts with naphthol or phenol or 3,4 substituted phenol for 30-60 min under a (C4H12N2)2[BiCl6]Cl.H2O catalysis condition without a solvent after heating to a temperature of 25-50 DEG C to produce a beta-alkoxy alcohol compound, wherein the (C4H12N2)2[BiCl6]Cl.H2O can be used a plurality of times after treatments such as filtration, washing and drying after completing the reaction. The process has advantages of short reaction time, good selectivity, environmental protection and high product yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis of organic intermediates, and the method can be applied in the process of preparing beta-alkoxy alcohol derivatives from epoxy compounds and phenols. Background technique [0002] β-alkoxy alcohols are an important class of organic compounds, which are widely used in the synthesis of β-alkoxy ketones, β-alkoxy acids and some natural products. β-alkoxy alcohols also play a vital role in medicinal chemistry, many medicines contain β-alkoxy alcohol compounds, for example, a fungal metabolite cyclosporine contains β-alkoxy The alcohol group is shown in Formula 1, which is a low-toxicity immune preparation and high-efficiency drug, and is currently successfully used as an anti-resistance drug in organ transplantation. Mandelic acid, which is widely used clinically, also contains β-alkoxyalcohol groups, and it is an antibacterial drug and oral antibiotic. The β-alkoxy alcohol group is also an importan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/03C07C43/253
Inventor 陆鸿飞孙磊磊高玉华蔡星伟周君涛杨飞飞乐文俊
Owner JIANGSU UNIV OF SCI & TECH
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