Guaiacol → 1-(2-Chloroethoxy)-2-methoxybenzene

Participants

Reaction Steps

A mixture of 52.88 g (0.426 mole) of guaiacol, 100 g (0.426 mole) of chloroethyl tosylate, 88.3 g (0.639 mole) of powdered potassium carbonate and 600 mL of 2-butanone is stirred mechanically and refluxed for 2 days. The reaction is filtered and the solid is rinsed with 2-butanone. The filtrate is evaporated and the residue taken up in ether and washed with 1N NaOH to remove unreacted guaiacol. The ether layer is dried over sodium sulfate, filtered and evaporated to give an oil which slowly crystallized. The solid is isolated with cold cyclohexane to give 41.47 g (52%) of 1-(2-Chloroethoxy)-2-methoxybenzene as a white solid, m.p. 42–3° C.

Provenance & Evidence