Malonic Acid → 4-Vinylguaiacol

Participants

Reaction Steps

A mixture of 4-hydroxy-3-methoxybenzaldehyde (3.42 mmol), malonic acid (13.68 mmol), piperidine (15.58 mmol) in DMF (20 ml) were taken in a 100 ml round bottom flask fitted with a condenser. The flask was shaken well and placed inside the monomode microwave oven and irradiated (250 W, 160° C.) for 15 minutes in parts. After completion, the reaction mixture was poured in ice cooled water and extracted with ethyl acetate. The organic layer was washed with dil. HCl, brine and water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain liquid which was purified on silica gel by column chromatography using a mixture of hexane and ethyl acetate (9:1 to 6:4), provided 4-hydroxy-3-methoxystyrene, a sweet and pleasant smelling liquid, in 51% yield; 1H NMR (CDCl3) 7.36 (21-1, d), 6.94 (2H, m), 6.83 (5H, m), 5.59 (1H, s), 3.86 (3H, s), 3.75 (3H, s); 13C NMR (CDCl3) 159.0, 146.7, 145.2, 130.3, 127.4, 126.6, 126.1, 120.1, 114.5, 114.1, 108.0, 55.9 and 55.3.

Provenance & Evidence