KR890003289B1 - Process for the preparation alpha-cyano-3-phenoxy-benzyl-s-(+)-2-(4chlorophenyl)-3-methyl buthylic acid - Google Patents

Abstract

A method for preparing α -cyano-3-phenoxybenzyl-S-(+)-2- (4chlorophenyl)-3-methylbathylate is presented. Thus organic material, β -phenoxybenzealdehyde and inorganic material, sodium cyanide are reacted and resulting compds. are reacted with S-(+)2- (4-chlorophenyl)-3-methylbutanoyl chloride.

Description

Preparation of α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutylate

The present invention relates to α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3- which is a pyrethroid insecticide which has little toxicity to plants and mammals and has excellent insecticidal effect. It relates to a process for preparing methyl butyrate without using a phase change catalyst.

Korean Patent Publication No. 82-772 and Belgian Kingdom Patent No. 801,946 describe the preparation of α-cyano-3-phenoxybenzyl-2- (4-chlorophenyl) -3-methyl-butylate, respectively. In addition, since all of them use phase change catalysts during the reaction, it is necessary to perform a cumbersome washing operation to remove the phase change catalysts after completion of the reaction, and it takes a long time, and it is impossible to expect satisfaction in terms of purity and yield.

Accordingly, an object of the present invention is to provide α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutyl in a short time with high purity and high yield without using a phase change catalyst. It is to provide a method for producing a rate.

The present invention, without using a phase change catalyst, the organic meta-phenoxybenzaldehyde and the inorganic sodium cyanide is reacted, and then the reaction product S-(+)-2- (4-chlorophenyl) -3-methyl It relates to a method for producing α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutylate by reacting butanoyl chloride.

In general, the compounds according to the invention are prepared with optically active acids, for example S-(+)-2- (4-chlorophenyl) -3-methylbutanoylchloride and alcohols, for example meta-phenoxybenzaldehyde Cyano hydrin can be prepared by esterification in a suitable inert solvent.

At this time, any inert solvent can be used, and benzene, toluene, hexane, heptane, xylene, pentane and the like are preferable.

The reaction uses a gas-liquid-solid three phase reactor. The reactor should be equipped with a gas introduction device capable of introducing air and inert gas for effective contact between organic and inorganic matters.

The reaction temperature and reaction time vary slightly depending on the type of solvent used. The reaction temperature is in the range of about 0 ° C. to 120 ° C., preferably between 10 ° C. and 65 ° C. and the reaction time is within 1 hour to 6 hours.

Since the phase change catalyst which dissolves in both an organic solvent and water is not used, after the completion of the reaction, it is not necessary to perform a cumbersome washing operation to remove the phase change catalyst.

In addition, the phase change catalyst not removed remains intact even when the solvent is distilled off under reduced pressure. Thus, α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutyl The purity of the rate is lowered.

Therefore, the preparation of α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutylate without using the phase change catalyst of the present invention is considered in various respects. Very advantageous.

It is also particularly advantageous at the reaction temperature because the reaction can proceed at room temperature.

Example 1

A thermometer, gas introduction tube, condenser and stirrer are attached to a three-phase reactor of gas-liquid-solid. 27.0 g of sodium cyanide and 70.5 g of water are added thereto, followed by stirring to dissolve sodium cyanide. 109.0 g of meta-phenoxy benzaldehyde and 512 g of noteheptane are added, and nitrogen gas is introduced at a flow rate of 300 ml / min. Stir vigorously at room temperature for 10 minutes. 127.1 g of S-(+)-2- (4-chlorophenyl) -3-methylbutanoyl chloride and 265 g of normal heptane are added thereto, and the mixture is stirred vigorously at room temperature for 1 hour. Wash twice with 400 ml of room temperature water. The solvent was distilled off under reduced pressure. 225.7 g of α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutylate having a purity of 95% was obtained.

Example 2

Attach the thermometer, gas introduction tube, condenser and stirrer to the gas-liquid-solid three-phase reactor. 17.2 g of sodium cyanide and 483 g of toluene were added thereto and stirred to dissolve sodium cyanide. 69.4 g of meta-phenoxybenzaldehyde and 84.9 g of S-(+)-2- (4-chlorophenyl) -3-methylbutanoyl chloride are added and air is introduced at a flow rate of 450 ml / min. Stir vigorously at 5 ° C. for 2 hours. Wash twice with 300 ml of 40-50 ° C. water. The solvent is distilled off under reduced pressure. 140.2 g of α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutylate having a purity of 93.5% was obtained.

As described above, since the method according to the present invention does not use a phase change catalyst, only the inorganic matters need to be removed after the reaction is completed. In this case, since the organic matters are washed 1-2 times with only water, the amount of waste water to be treated is very small. There is an advantage.

Claims (1)

After reacting the organic meta-phenoxybenzaldehyde and the inorganic sodium cyanide, the reaction product is reacted with S-(+)-2- (4-chlorophenyl) -3-methylbutanoyl chloride to produce α-cyano-3 -In preparing phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutylate, it is characterized in that a phase shift catalyst is not used as a reaction solvent in a mixture of water and a non-polar solvent. Α-cyano-3-phenoxybenzyl-S-(+)-2- (4-chlorophenyl) -3-methylbutylate.