JPS58152855A - Preparation of lower alkoxybenzonitrile - Google Patents

Abstract

PURPOSE:To prepare the titled compound useful as a perfume, etc., in high yield and purity, by reacting a hydroxybenzonitrile which may have other substituent group on the benzene ring with di(lower alkyl) sulfate in the presence of an alkali. CONSTITUTION:A hydroxybenzonitrile which may have other substituent group (e.g. halogen, nitro, etc.) on the benzene ring is made to react with a di(lower alkyl) sulfate (e.g. dimethyl sulfate, diethyl sulfate, etc.) in the presence of an alkali such as alkali hydroxide, in an inert solvent such as xylene. Although the reaction proceeds at a low temperature, it is preferable to heat the reaction system at the boiling temperature of the reaction mixture for the rapid reaction, and the reaction completes within about 1-10hr. EFFECT:The objective compound can be prepared by a simple procedure, and the process has high industrial value.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to improvements in the process for producing lower alkoxybenzonitrile.

Lower alkoxybenzonitrile is used in perfumes, liquid crystals, etc., and is also useful as a raw material for the synthesis of oxazoles. The only known method for synthesizing this compound is from a lower alkoxybenzene derivative. Recently, it has become possible to easily obtain oxybenzoic acid (oxypenzoni)IJ sils from oxybenzoic acid or its esters, so the present inventors investigated the lower alkoxylation thereof. Generally, benzene) IJ sils are sensitive to strong acids or bases, so
Difficulties are expected in lower alkylating the hydroxyl group. However, as a result of research, the present inventors overcame the anticipated difficulties and achieved the present invention by appropriately combining di-lower alkyl sulfuric acid and an alkali.

The present invention is a method for producing lower alkoxybenzonitrile, which is characterized by reacting oxybenzonitrile, which may have other substituents on the benzene nucleus, with di-lower alkyl sulfuric acid in the presence of an alkali. .

Examples of substituents that may be present on the benzene nucleus of oxybenzonitrile include a halogen atom, a lower alkyl group, a lower alkoxy group, and a nitro group. - As the di-lower alkyl sulfuric acid, dimethyl sulfate, diethyl sulfate, dipropyl sulfate, cyamyl sulfate, etc. are used. Preferred examples of the alkali include alkali hydroxide, alkali carbonate, alkali hydrogen carbonate, and alkali phosphate.

In carrying out the invention, it is advantageous to react the oxybenzonitrile and di-lower alkyl sulfuric acid in a solvent in the presence of an alkali. In addition to water, solvents include common inert solvents such as xylene. Toluene, benzene, etc.

In a preferred embodiment of the present invention, oxybenzonitrile is dissolved in an aqueous alkali hydroxide solution at a low temperature,
Dialkyl sulfuric acid is added dropwise to this, and then heated under reflux. Alternatively, oxybenzonitrile and alkali carbonate,
For example, the mixture may be heated under reflux in an inert solvent such as xylene, and di-lower alkyl sulfuric acid may be added dropwise to react.

After the reaction is completed, the precipitated target product is collected or the solvent is distilled off to separate the target product. If necessary, the target product can be purified by recrystallization, distillation, etc.

According to the method of the invention, lower alkoxybenzoni) I
Since it can be obtained in high yield and purity using a simple and simple method, its industrial value is extremely high.

Example 1 595 g of roseoxybenzonitrile is stirred and dissolved in a solution of 20 g of sodium hydroxide and 200 ml of water, and the solution is cooled to below 10°C. Then under cooling dimethyl sulfate 75.6
g was added dropwise and heated under reflux for 6 hours. After the reaction is completed, the precipitated crystals are cooled and P is removed.
158.59 (yield 88.0%) is obtained.

Example 2 595 g of roseoxybenzonitrile and 100 I of carbonic acid are added to 600 g of xylene, and the mixture is heated to reflux while stirring. Next, 79.8.9 mm of dimethyl sulfate was added dropwise over 1 hour, and the mixture was heated and stirred under reflux for 6 hours. After the reaction is complete, cool and read carefully until the xylene solution becomes neutral. Next, xylene is distilled off under reduced pressure to obtain 64.1 g (yield 96.4%) of rose anisonitrile.

Example 6 In Example 2, 59.5 g of saliteronitrile # was used instead of roseoxybenzonitrile, and 97.59 g of diethyl sulfate was used instead of dimethyl sulfate, and the following Example 2 was carried out.
By operating in the same manner as above, 2-ethoxybenzonitrile 69
．． 89 (yield 95.0%) is obtained.

Applicant: Ueno Pharmaceutical Application Research Institute Co., Ltd. Agent: Patent Attorney Masao Kobayashi

Claims (1)

[Claims] A method for producing lower alkoxybenzonitrile, which comprises reacting oxybenzonitrile which may have other substituents on the benzene nucleus with di-lower alkyl sulfuric acid in the presence of an alkali.