Allyl bromide → Ethyl 4-(prop-2-en-1-yloxy)benzoate

Participants

Reaction Steps

To a stirred solution of 66.4 g (0.4 mole) ethyl 4-hydroxybenzoate in 100 ml acetone, under a nitrogen atmosphere was added 55.3 g (0.40 mole) finely powdered potassium carbonate and 53.2 g (0.44 mole) allyl bromide and the resulting mixture was heated at reflux overnight. After cooling to room temperature the mixture was filtered, washing with ethyl ether. The filtrate and washings were washed with water, brine and dried (MgSO4). Evaporation of solvent in vacuo gave 82.3 g of product as a clear oil. 1H-NMR(CDCl3)ppm(delta): 5.0-5.5 (m), 5.8 (m), 6.8 (m), 8.0 (m).

Provenance & Evidence