Water → Vanillin

참여 물질

반응 단계

The obtained 4-hydroxy, 3-methoxystyrene was taken in a 100 ml round bottom flask fitted with a condenser and mixed with para-iodo anisole (1.9 mmol), piperidine (4.5 mmol), palladium acetate (0.076 mmol), triphenylphosphine (0.089 mmol) and DMF (20 ml). The flask was shaken well and placed inside the monomode microwave oven and irradiated (250 W, 160° C.) for 30 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 a white solid; 50% yield (20% overall yield starting from vanillin) (m.p. 163-166° C.); 1H NMR (CDCl3) δ 7.37 (2H, d), 6.95 (2H, d,), 6.84 (5H, m), 3.88 (3H, s), 3.76 (3H, s); 13C NMR (CDCl3) δ 159.0, 146.7, 145.3, 130.4, 127.4, 126.6, 126.1, 120.1, 114.5, 114.1, 108.0, 55.9 and 55.3.

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