Allyl bromide → Ethyl 4-allyloxyphenoxyacetate

Participants

Reaction Steps

Allyl bromide (3.37 g) was added to a stirred suspension of ethyl 4-hydroxyphenoxyacetate (5.14 g) [prepared by method of Moser, J.A.C.S., (1950), 72, 1413) and potassium carbonate (3.90 g) in butan-2-one (50 ml). The reaction mixture was heated at reflux for 12 hours. The reaction mixture was cooled to ambient temperature and then filtered. The filtrate was evaporated to give an oil which was purified by column chromatography on silica gel (Merck. Art. No. 7734) using a 4:1 (v/v) mixture of hexane and ethylacetate as eluent to give ethyl 4-allyloxyphenoxyacetate (6.41 g) as a colourless oil; microanalysis, found: C, 65.8; H, 7.20%; C13H16O4 requires C, 66.1; H, 6.83%; NMR (CDCl3): 1.28 (3H, t), 4.25 (2H, q), 4.48 (2H, m), 4.57 (2H, s), 5.22-5.44 (2H, m), 5.92-6.12 (1H, m) and 6.84 (4H, s).

Provenance & Evidence