Vanillin → 4-Cyclopentyloxy-3-methoxy-benzaldehyde

Participants

Reaction Steps

A mixture of vanillin (10 g, 65.7 mmoles), cyclopentyl bromide (21.09 g, 196.7 mmoles), tetrabutylammonium bromide (211.8 mg, 0.675 mmoles) and K2CO3 (27.16 g, 199.48 mmoles) in tetrahydrofuran/water 8:2 (200 ml) was refluxed under nitrogen and vigorous stirring for 55 hours, then diluted with water, extracted with ethyl acetate, and the extract was washed with water, anhydrified over Na2SO4 and dried to give an oil which was purified by silica gel flash chromatography (eluent: petrolatum/ethyl acetate 9:1) and gave 14 g of the title product (yield: 97%).

Provenance & Evidence