Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-hydroxy-4-methoxybenzaldehyde (40 g, 0.26 mol), potassium carbonate (40 g, 0.29 mol) and bromocyclopentane (32 ml, 0.31 mol) in dimethylformamide (0.25 l) was heated under an argon atmosphere at 100° C. After 4 hours, additional bromocyclopentane (8.5 ml, 0.08 mol) was added and heating was continued for 4 hours. The mixture was allowed to cool and was filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between ether and aqueous sodium bicarbonate. The organic extract was washed with aqueous sodium carbonate and was dried (potassium carbonate). The solvent was removed in-vacuo and the residue was purified by flash chromatography, eluting with 2:1 [may also be distilled at ~0.02 mm Hg] hexanes/ether to provide a pale yellow oil (52 g, 89%).

Provenance & Evidence