Nitric Acid → Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 100 g (386.5 mmol) 4-(3-chloro-propoxy)-5-methoxy-benzoic acid methyl ester in 300 ml acetic acid was added dropwise 100 ml of 70% nitric acid. The mixture was heated to 50° C. for 1 hr and then poured into ice water. The mixture was extracted with chloroform. The organic solution was washed with dilute sodium hydroxide and then dried over magnesium sulfate. The solvent was removed. Ether was added an the mixture was stirred until solid was deposited. The solid was collected by filtration giving 98 g of 4-(3-Chloro-propoxy)-5-methoxy-2-nitro-benzoic acid methyl ester as white crystals: mass spectrum (electrospray, m/e,): M+H 303.8; 2M+NH4 623.9.

Provenance & Evidence