N,N-Dimethylaniline → Ethyl 3-allyl-4-hydroxybenzoate

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Reaction Steps

A mixture of 82.3 g (0.899 mole) ethyl 4-allyloxybenzoate in 100 ml N,N-dimethylaniline was stirred under nitrogen while heating at reflux for 2 days. The resulting mixture was cooled to room temperature, the solvent distilled in vacuo, the residue taken up in ethyl ether, washed three times with 1N hydrochloric acid and extracted with 1N sodium hydroxide solution. The alkaline extract was acidified to pH 3.0, extracted with ethyl ether and the extracts dried (MgSO4). Evaporation of solvent provided 47.1 g of the desired product as a solid, TLC with 1.5:1 isopropyl ether/hexane gave one spot, Rf 0.2.

Provenance & Evidence