4-Hydroxybenzaldehyde → 4-(Cyclohexylmethoxy)benzaldehyde

Participants

Reaction Steps

A mixture of 4-hydroxybenzaldehyde (1.22 g, 10.0 mmol), K2CO3 (1.45 g, 10.5 mmol), and bromomethylcyclohexane (1.54 mL, 11.0 mmol) in CH3CN (20 mL) was stirred at reflux for three days. The reaction mixture was then cooled, poured into 1 M aq NaOH and extracted with Et2O. The extract was washed with H2O and brine. The aqueous washes were reextracted once with Et2O, and the combined extracts were dried over MgSO4 and concentrated to 2.03 g (93%) of ether as a solid. This material was used without further purification.

Provenance & Evidence