p-METHOXY-alpha-METHYLCINNAMALDEHYDE → 3-Hydroxy-1-(4-methoxyphenyl)-2-methylpent-1-ene

Participants

Reaction Steps

To a solution of 3-(4-methoxyphenyl)-2-methylpropenaldehyde (10.3 g, 0.058 mol) in dried diethyl ether (150 ml) cooled to −15° C. and stirred under an atmosphere of nitrogen was added a solution of ethylmagnesium bromide in diethylether (3M, 21.4 ml). The reaction mixture was allowed to warm to room temperature and after ½ hour poured onto ice cold aqueous hydrochloric acid (2M, 50 ml). The organic phase was separated, washed with water, a saturated solution of sodium bicarbonate and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to give 3-hydroxy-1-(4-methoxyphenyl)-2-methylpent-1-ene as a yellow oil.

Provenance & Evidence