KR900008127B1 - Process for the preparation of 3-phenoxybenzyl-2(4-alkoxyphenyl)-2-methyl propyleter - Google Patents

Abstract

3-Phenoxybenzyl-2-(4-alkoxyphenyl)-2methylpropyl ether of formula (I) are prepared by reacting 2-(4-alkoxyphenyl)-2methylpropylalcohol with 3-phenoxybenzyl sulfonate in the presence of a base and aromatic hydrocarbon. In (I), R= methyl or ethyl; R'= p-toluenesulfonyl, methylsulfonyl or 2,4,6-trimethylbenzene sulfonyl. (I) are useful as insecticides.

Description

Method for preparing 3-phenoxybenzyl 2- (4-alkoxyphenyl) -2-methylpropyl ether

The present invention relates to a novel process for preparing 3-phenoxybenzyl 2- (4-alkoxyphenyl) -2-methylpropyl ether represented by the following general formula (I).

In the formula, R represents a methyl or ethyl group.

Generally, 3-phenoxybenzyl 2- (4-alkoxyphenyl) -2-methylpropyl ether represented by the general formula (I) is a pesticide with excellent insecticidal properties, and according to Japanese Patent Application No. 56-154427, In addition to insecticidal properties, it has been known to have acaricidal activity, fast-acting activity and residual activity, and has a broad insecticidal spectrum showing little residual toxicity in humans as well as land animals and fish.

On the other hand, in British Patent No. 2,131,424A, a method for producing 3-phenoxybenzyl 2- (4-alkoxyphenyl) -2-methylpropyl ether represented by the general formula (I), It is proposed to reduce the 3-phenoxybenzyl 2- (4-alkoxy-3-chlorophenyl) -2-methylpropyl ether represented by high pressure reaction with palladium / carbon (Pd / C) in the presence of a base. .

(가)

(end)

Wherein R is as defined above.

In addition, Japanese Patent No. 58-32840 discloses the reaction of 2- (4-alkoxyphenyl) -2-methylpropyl alcohol with 3-phenoxybenzyl bromide represented by the following general formula (B) in the presence of a strong base. A method for preparing the compound represented by I) is described.

(나)

(I)

However, in the case of preparing the compound represented by the general formula (I) according to the conventional method as described above, it is not only economical, such as the use of expensive catalysts, the production of many side reactions and low yield, but also it is impossible to industrialize. It was hard to do.

Accordingly, an object of the present invention is to provide an economical method for preparing 3-phenoxybenzyl 2- (4-alkoxyphenyl) -2-methylpropyl ether of formula (I) in high yield and high purity in a short time under mild conditions. To provide a method.

Hereinafter, the present invention will be described in detail.

The present invention relates to the preparation of 3-phenoxybenzyl 2- (4-alkoxyphenyl) -2-methylpropyl ether represented by the following general formula (I), which is represented by the following general formula (II). Alkoxyphenyl) -2-methylpropyl alcohol is prepared by reacting with 3-phenoxybenzyl sulfonate represented by the following general formula (III) in the presence of a base and an aromatic hydrocarbon solvent.

In the above formulas, R represents a methyl or ethyl group, and R 'represents a p-toluenesulfonyl, methylsulfonyl or 2,4,6-trimethylbenzenesulfonyl group.

Hereinafter, the present invention will be described in more detail.

2- (4-ethoxyphenyl) -2-methylpropyl alcohol represented by the general formula (II) used as the starting material of the present invention may be prepared according to the method described in US Pat. No. 4,397,864.

Suitable bases for use in the present invention include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium oxide, sodium carbonate or magnesium hydroxide, preferably sodium hydroxide or potassium hydroxide, the amount of which is used above It is good to set it as 1.0-10.0 mol times with respect to the compound of general formula (II), Preferably it is 1.0-5.0 mol times.

Aromatic hydrocarbon solvents suitable for use in the present invention include benzene, toluene, xylene, and the like. The 3-phenoxybenzyl sulfonate compound of the general formula (III) used in the present invention is represented by the general formula (II). It is preferable to use 0.95 to 1.5 mole times, preferably 1.0 to 1.1 mole times with respect to the chemical of

On the other hand, the present invention as described above can be easily carried out in the temperature range of 0 ℃ to 150 ℃, preferably 10 ℃ to 110 ℃ is suitable.

In preparing the compound of Formula (I) according to the present invention, when the reaction is carried out in the range other than the above reaction conditions, the production of the side reaction products is increased accordingly, and the yield of the desired product is reduced. Not preferred.

Hereinafter, the present invention will be described in more detail with reference to Examples.

Production Example

Preparation of 3-phenoxybenzyl p-toluenesulfonate

3-phenoxybenzyl alcohol (120.4 g, 0.61 mole), p-toluenesulfonyl chloride (124 g, 0.64 mole) and sodium hydroxide (36.4 g, 0.92 mole) are stirred with 700 ml of toluene at room temperature for 5 hours.

Subsequently, the reaction solution is washed with 500 ml of H ₂ O, the organic layer is separated, and the aqueous layer is extracted with 200 ml of toluene and combined with the toluene layer.

Thereafter, the organic layer was dried with MgSO ₄ 200 mg, filtered and concentrated to obtain 210 g of a white solid powder (yield 98%, purity 99%).

Example 1

Preparation of 3-phenoxybenzyl 2- (4-ethoxyphenyl) -2-methylpropyl ether

2- (4-ethoxyphenyl) -2-methylpropyl alcohol (19.4 g, 0.10 mole), 3-phenoxybenzyl P-toluene sulfonate (35.4 g, 0.10 mole), potassium hydroxide (23.8 g, 0.41 mole) and 400 ml of toluene are added and stirred at room temperature for 5 hours. Thereafter, the mixture was washed with 500 ml of water in a separatory funnel, and the organic layer was separated. The separated organic layer was dehydrated with 15 g of MgSO ₄ , filtered and distilled under reduced pressure to obtain 37.0 g (yield 98.5%) of the target compound.

Purity (gas chromatography, area%): 97.5%

Example 2

Preparation of 3-phenoxybenzyl 2- (4-methoxyphenyl) -2-methylpropyl ether

The procedure of Example 1 was repeated except that 2- (4-methoxyphenyl) -2-methylpropyl alcohol was used instead of 2- (4-ethoxyphenyl) -2-methylpropyl alcohol. 35.2 g (97.50% yield) of 3-phenoxy benzyl 2- (4-methoxyphenyl) -2-methylpropyl ether were prepared.

Purity (gas chromatography, area%): 98.0%

Claims (6)

In preparing 3-phenoxybenzyl 2- (4-alkoxyphenyl) -2-methylpropyl ether represented by the following general formula (I), 2- (4-alkoxyphenyl) represented by the following general formula (II) 3-phenoxybenzyl 2- (4-alkoxy) characterized by reacting 2-methylpropyl alcohol with 3-phenoxybenzyl sulfonate represented by the following general formula (III) in the presence of a base and an aromatic hydrocarbon solvent: Method for preparing phenyl) -2-methylpropyl ether.

In the above formulas, R represents a methyl or ethyl group, and R 'represents a p-toluenesulfonyl, methylsulfonyl, or 2,4,6-trimethylbenzenesulfonyl group. The method of claim 1 wherein the aromatic hydrocarbon solvent is benzene, toluene or xylene. The method of claim 1, wherein the base is sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, sodium oxide, sodium carbonate or magnesium hydroxide. The method of claim 1, wherein the base is used in an amount of 1.0 to 10.0 mole times with respect to the compound of formula (II). The method of claim 1, wherein the amount of the compound represented by the general formula (III) is 0.95 to 1.5 mole times with respect to the compound represented by the general formula (II). The method of claim 1, wherein the reaction is carried out at a temperature of 0 ℃ to 150 ℃.