Isovanillin → (E)-3-Hydroxy-4,4'-dimethoxystilbene

Participants

Reaction Steps

To a stirred mixture of 4-methoxybenzyltriphenylphosphonium chloride (5.51 g, 13mmol) and 4-methoxy-3-hydroxybenzaldehyde (2 g, 13 mmol) in CH2Cl2 was added a cooled aqueous solution of NaOH(62.5 eq) in H2O. The mixture was stirred at room temperature for 48 h. The aqueous layer was then acidified to pH 5 and the precipitated solid was filtered and dried. Purification by silica gel chromatography using hexane/ethyl acetate (1:1) gave the title E-trans product as a colourless solid 0.11 g (3%): 1H NMR (DMSO) δ 9.3 (1H, bs). 7.6 (2H, d), 7.2 (7H, m), 3.5 (6H, s): Mass Spectrum (FAB) 257 (M+1).

Provenance & Evidence