4-Hydroxybenzaldehyde → 4-(Cyclohexylmethoxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 4-hydroxybenzaldehyde (0.244 g, 2.00 mmol) in CH3CN (4.0 mL) was treated with bromomethylcyclohexane (0.279 g, 2.00 mmol) and K2CO3 (0.332 g, 2.40 mmol). The reaction mixture was heated to 100° C. for 1 h in a Biotage Initiator microwave synthesizer. Additional bromomethylcyclohexane (0.279 g, 2.00 mmol) and K2CO3 (0.332 g, 2.40 mmol) were added and the reaction mixture was again heated to 100° C. for 1 h in a Biotage Initiator microwave synthesizer. Additional bromomethylcyclohexane (0.279 g, 2.00 mmol) and K2CO3 (0.332 g, 2.40 mmol) were added and the reaction mixture was again heated to 100° C. for 1 h in a Biotage Initiator microwave synthesizer. Following cooling, the reaction mixture was filtered and concentrated in vacuo. Purification via flash column chromatography (10% EtOAc/hexanes) gave the title compound as a white solid (0.360 g; 82%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.86 (s, 1 H) 7.85 (d, J=8.8 Hz, 2 H) 7.11 (d, J=8.8 Hz, 2 H) 3.89 (d, J=6.3 Hz, 2 H) 1.80 (d, J=12.6 Hz, 2 H) 1.61-1.79 (m, 4 H) 1.13-1.32 (m, 3 H) 1.07 (dd, J=12.6, 2.6 Hz, 1 H) 1.01 (dd, J=11.9, 2.5 Hz, 1 H). MS(ES+) m/e 219 [M+H]+.

Provenance & Evidence