Water → Isopropyl 4-chloro-3-nitrobenzoate

Participants

Reaction Steps

To a stirred solution of 4-chloro-3-nitrobenzoyl chloride (20.5 g) in ethyl acetate (80 cm3) was added a solution of triethylamine (10.1 g) and i-propylalcohol (6 g) in ethylacetate (40 cm3) over 15 mins causing a slight exotherm. The reaction was stirred at the ambient temperature for a further 3.5 hours and then poured into water. The layers were separated and the aqueous layer was extracted with ethyl acetate and the combined ethyl acetate layers were washed with 10% HCl, brine and dried with sodium sulphate. Filtration and evaporation gave iso-propyl 4-chloro-3-nitrobenzoate as a yellow solid (22.5 g). 1H nmr (CDCl3) d: 8.49 (1H, d), 8.17 (1H, dd), 7.64 (1H, d), 5.29 (1H, septet), 1.40 (6H, d). Mpt 61°-62° C.

Provenance & Evidence