4-Hydroxybenzaldehyde → Phenol, 4-(dimethoxymethyl)-

Participants

Reaction Steps

A mixture of 4.88 g (40 mmol) of 4-hydroxybenzaldehyde, 6.6 g (206 mmol) of methanol and 5.1 g (48 mmol) of trimethylorthoformate and 28 mg of p-toluene sulfonic acid was stirred at room temperature for 12 h. An excess of NaHCO3 was then added and the mixture stirred for a further 60 h. The mixture was then filtered, the solvent removed in-vacuo and the residue purified by flash chromatography (silica; 20% ethyl acetate in hexanes) to give the title compound as a viscous oil.

Provenance & Evidence