Tetrahydrofuran → 2-Methoxy-4-(3-oxoprop-1-en-1-yl)phenyl acetate

Participants

Reaction Steps

Acetoxy vanillin (5.0 g, 2.6×10-2M) is dissolved in dry THF (300 ml) with formyl methylenetriphenylphosphorane (78 g, 2.6×10-2M) and refluxed under an atmosphere of argon for 80 hours. The reaction mixture is concentrated to dryness and chromatographed on flash silica to afford 4-acetoxy-3-methoxycinnamaldehyde (3 g, 54% yield); mp=83°-86° C.

Provenance & Evidence