Acetic Anhydride → 2-Cyano-4-nonylphenyl acetate

Participants

Reaction Steps

A solution of 52.6 parts of 2-hydroxy-5-nonyl-benzaldoxime (in which the nonyl group is a mixture of branched chain isomers; prepared as described in Example 1 of Belgian Pat. No. 796835) in 60 parts of acetic anhydride was stirred and boiled for 1 hour. The cooled solution was poured into water, stirred for 30 minutes and extracted into 2 × 150 parts of chloroform. The extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated at 50° C under vacuum to yield 61.6 parts of 2-acetoxy-5-nonylbenzonitrile as a brown oil. The 61.6 parts of the acetoxy compound were mixed with 200 parts of ethanol and 300 parts of a 2N solution of sodium hydroxide and the mixture stirred and boiled under reflux for 11/2 hours. The cooled solution was acidified with hydrochloric acid, diluted with water and extracted into chloroform. The extracts were water washed, dried over anhydrous magnesium sulphate and evaporated to give 53.1 parts of 2-hydroxy-5-nonylbenzonitrile as a brown oil.

Provenance & Evidence