Phenolate Sodium → Ethyl 2-methoxy-5-phenoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 5-iodo-2-methoxybenzoate (4.1 g, 13.4 mmol), sodium phenoxide (1.7-1.8 g, 15 mmol), copper(I) oxide (1.1 g, 7.5 mmol) and dimethylacetamide (approximately 15 mL) was heated 4 hours with stirring at 180° C. The mixture was filtered, diluted with water and extracted with pentane/diethyl ether (7:3, 2× 100 mL). The combined extracts were washed with dilute sodium hydroxide (3×) and water (1×), dried (K2CO3), filtered and concentrated. The residue was dried (P2O5) under vacuum to give crude product (1.17 g) which was combined with crude product (2.4 g) similarly prepared from methyl 5-iodo-2-methoxybenzoate (6 g, 19.6 mmol). The combined crude product was purified by column chromatography eluting with hexane/acetone (96:4) to give ethyl 2-methoxy-5-phenoxybenzoate (2 g, 7.3 mmol), m.p. 52°-52° C.

Provenance & Evidence