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Cholromethylation method of benzoic acid derivative

A technology for chloromethylation and derivatives, applied in the field of chloromethylation of benzoic acid derivatives, can solve problems such as inability, research, and long reaction steps

Inactive Publication Date: 2011-10-05
HUBEI XUNDA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The chloromethylation reaction on the inactive benzene ring (aromatic ring) is often impossible or difficult to carry out. Because of this, the methodology and technology of the chloromethylation reaction on the inactive benzene ring (aromatic ring) have not been studied deeply.
Because we need intermediates such as methyl 3-chloromethylbenzoate, but according to the general method, the reaction steps are long and the cost is high, so we have studied in detail the chloromethylation reaction on the inactive benzene ring (aromatic ring)

Method used

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  • Cholromethylation method of benzoic acid derivative
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  • Cholromethylation method of benzoic acid derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1: Chloromethylation of methyl benzoate

[0025] Add 50ml of methylene chloride, 26 grams (0.19mol) of aluminum trichloride and 3.0 grams (0.1mol) of paraformaldehyde in a 100ml three-necked flask, add 13.6 grams (0.1mol) of methyl benzoate dropwise under stirring, and then reflux reaction After 10 hours, the reactant flow was added to 100 g of ice water, stirred for 30 minutes, separated into layers, the water layer was extracted with 20 ml of dichloromethane, the organic layers were combined, washed twice with 10 ml of water, concentrated to recover dichloromethane, the residue was 16.5 g, According to HPLC analysis, it contained 80% of methyl 3-chloromethyl benzoate, 5% of unreacted methyl benzoate, and 15% of other impurities.

Embodiment 2

[0026] Example 2: Chloromethylation of methyl benzoate

[0027] Add 50ml of chloroform, 26.5g (0.2mol) of aluminum trichloride and 1.5g (0.05mol) of paraformaldehyde into a 100ml three-necked flask, stir and cool to below 10°C, and dropwise add 13.6g (0.1mol) of formaldehyde benzoate ester, then react at 50°C for 8 hours, add the reactant stream to 100 g of ice water, stir for 30 minutes, separate layers, add 20 ml of chloroform to the water layer for extraction, combine the organic layers, wash twice with 10 ml of water, concentrate and recover chloroform , 15.2 g of the residue, analyzed by HPLC, contained 50% of methyl 3-chloromethyl benzoate, 35% of unreacted methyl benzoate, and 15% of other impurities.

Embodiment 3

[0028] Example 3: Chloromethylation of Benzonitrile

[0029] In 100ml there-necked flask, add 50ml chloroform, 25 grams (0.189mol) aluminum chloride and 2.8 grams (0.093mol) paraformaldehyde, add 10 grams (0.097mol) benzonitrile under stirring, then reflux reaction 15 hours, will The reaction stream was added to 100 g of ice water, stirred for 30 minutes, separated into layers, the water layer was extracted with 54 ml of chloroform, the organic layer was combined, washed twice with 10 ml of water, concentrated to recover chloroform, and the residue 14.5 g was analyzed by HPLC, which contained 3-chloro Tolunitrile 73%, unreacted benzonitrile 17.2%, other impurities 9.8%.

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Abstract

The invention relates to a cholromethylation method of a benzoic acid derivative, specifically comprising the step of making benzoate, benzamide, cyanobenzene and benzophenone react with paraformaldehyde and aluminium choride to generate a meta-position chloromethyl substituted benzoic acid derivative. The meta-position chloromethyl substituted benzoic acid derivative is an important intermediatefor fine chemicals, pesticides and medicines.

Description

technical field [0001] The invention relates to a method for chloromethylation of benzoic acid derivatives, that is, a method for preparing 3-chloromethylbenzoic acid derivatives through chloromethylation of benzoic acid derivatives. Background technique [0002] 3-Chloromethylbenzoic acid derivatives are very useful pharmaceutical intermediates and can be used to synthesize many products. At present, the synthetic methods of 3-chloromethylbenzoic acid derivative series products almost all start from m-xylene, generate 3-methylbenzoic acid through mono-oxidation, and then undergo monochlorination to generate 3-chloromethylbenzoic acid. These derivatives are then prepared. However, the selectivity of the above-mentioned monooxidation and monochlorination is not good, which eventually leads to a relatively complicated production process of 3-chloromethylbenzoic acid derivatives and high cost. [0003] US Patent No. 4,562,280 discloses a method for the chloromethylation of ar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/50C07C253/30C07C69/78C07C67/343C07C233/65C07C231/12C07C49/813C07C45/72
Inventor 易章国
Owner HUBEI XUNDA PHARMA