Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a magnetically-stirred solution of isovanillin (0.557 mol, 85.0 g) in dry dimethylformamide (500 mL) at room temperature was added powdered K2CO3 (0.558 mol, 77.1 g) in one portion followed by dropwise addition of neat cyclopentyl bromide (0.614 mol, 91.5 g; 65.9 mL). The resulting suspension is warmed to 60° C. and the reaction monitored by TLC until complete. Upon completion, the reaction mixture is cooled to room temperature and the dimethylformamide removed in vacuo. The residue is partitioned between water and ethyl acetate, the aqueous phase extracted with ethyl acetate and the combined organic layers are washed with water. The organics are dried (Na2SO4) and concentrated in vacuo to afford the alkylated product (0.317 mmol, 70.1 g; 57%) as a viscous oil which is of sufficient purity to be used as such in subsequent transformation.

Provenance & Evidence