Formaldehyde → 3-(1-Hexenyl)-2-hydroxybenzaldehyde

Participants

Reaction Steps

To a stirred solution of Mg(OMe)2 (8% by weight in methanol 16.88 ml, 12.76 mM) was added 2-(1-hexenyl)phenol (3.44 g, 19.5 mmol) in toluene (18 ml). The reaction mixture was warmed to reflux and held at reflux for 2 hours. Toluene (18 ml) was added and the solvent distilled off until the reaction temperature rose to 93° C. A slurry of paraformaldehyde (1.8 g, 60 mmol) in toluene (18 ml) was added and the reaction heated at reflux for 3 hours. The reaction was allowed to cool to ambient temperature and stirred overnight. The reaction was diluted with toluene (20 ml) and washed with 2M aqueous H2SO4 (20 ml). The organic phase was washed with water until the aqueous phase was neutral in pH, dried (MgSO4) and evaporated. The residue was purified by chromatography (eluant: ethyl ether/hexane) to give 3-(1-hexenyl)-2-hydroxybenzaldehyde (2.32 g, 58%).

Provenance & Evidence