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Method for preparing 3-cyano-4-isopropoxybenzoic acid

A technology of isopropoxybenzoic acid and ethyl isopropoxybenzoate, which is applied in the field of preparing 3-cyano-4-isopropoxybenzoic acid, can solve the problems of great harm, and is suitable for mass production , The cost advantage is obvious, and the raw materials are cheap and easy to obtain

Inactive Publication Date: 2017-05-17
SUZHOU BLUEHILL BIOPHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The biggest defect of this process is that cuprous cyanide, a highly toxic cyanide, is used in the process, which is relatively harmful in the actual market.

Method used

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  • Method for preparing 3-cyano-4-isopropoxybenzoic acid
  • Method for preparing 3-cyano-4-isopropoxybenzoic acid
  • Method for preparing 3-cyano-4-isopropoxybenzoic acid

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Embodiment

[0019] 1) Add ethyl p-hydroxybenzoate (2.75kg, 16.4mol), magnesium chloride (3.2kg, 32.8mol), triethylamine (9.3L, 82mol), paraformaldehyde (3.9kg, 131.2mol) into the 50L reaction pot ), dichloromethane (18L), heated in an oil bath at 60°C (inner temperature 44°C) overnight. After cooling to room temperature, slowly add 5 L of concentrated hydrochloric acid diluted aqueous solution, filter off the insoluble matter, extract with DCM 4 times, dry over sodium sulfate, filter and spin dry. directly to the next step.

[0020] 2) Add the raw materials of the previous step into the 50L reaction pot, hydroxylamine hydrochloride (1.14kg) and acetonitrile / N,N-dimethylformamide (10L / 2.5L), add acetyl chloride (1.17L), heat and stir at 80°C for 2 hours . After cooling to room temperature, add 10L of EA, wash with 5L of water twice, reverse extraction with water once, combine the organic layers, dry over sodium sulfate, filter, spin until half dry, a large amount of solid precipitates, d...

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Abstract

The invention discloses a method for preparing 3-cyano-4-isopropoxybenzoic acid, comprising the following steps: step 1, preparing 3-aldehyde-4-ethyl hydroxybenzoate from ethyl p-hydroxybenzoate; step 2, preparing 3-cyano-4-ethyl hydroxybenzoate from the 3-aldehyde-4-ethyl hydroxybenzoate; step 3, preparing 3-cyano-4-ethyl isopropoxybenzoate from the 3-cyano-4-ethyl hydroxybenzoate; and step 4, preparing 3-cyano-4-isopropoxybenzoic acid from the 3-cyano-4-ethyl isopropoxybenzoate. The method for preparing the 3-cyano-4-isopropoxybenzoic acid has the following advantages: (1) use of virulent cyanide, namely cuprous cyanide in the prior art is avoided, so the method is more suitable to be industrialized; (2) cyano groups are prepared from aldehyde groups, which is efficient, direct and suitable for mass production; and (3) all the raw materials are cheap and easily available and have obvious advantages in cost.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for preparing 3-cyano-4-isopropoxybenzoic acid. Background technique [0002] The traditional process for preparing 3-cyano-4-isopropoxybenzoic acid is as follows: [0003] [0004] The relatively big defect that this process exists is that the cuprous cyanide of highly toxic cyanide has been adopted in the process of the process, which has relatively large harm in the actual market. Contents of the invention [0005] The object of the present invention is to provide a kind of method for preparing 3-cyano group-4-isopropoxybenzoic acid, aims to solve the above problems. [0006] In order to achieve the above object, the technical scheme of the present invention is to design a method for preparing 3-cyano-4-isopropoxybenzoic acid, comprising the steps of: [0007] 1) Add magnesium chloride, triethylamine, paraformaldehyde, and dichloromethane to ethyl p-h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/57
CPCC07C67/313C07C253/00C07C253/30C07C253/34C07C255/57C07C69/84
Inventor 池永贵黄轩
Owner SUZHOU BLUEHILL BIOPHARMA CO LTD
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