2-Methylimidazole → 5-Ethenyl-2-methoxyphenol

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Reaction Steps

A mixture of Ferulic acid (0.0083 mol), KOH (10%, 3 ml), methylimidazole (1 mL) and dimethylformamide (10 ml) were taken in a 100 ml round bottom flask fitted with reflux condenser. The flask was placed inside the microwave oven and irradiated (150 W, 150° C.) for 12 minutes. The cooled mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with dil HCl, water, saturated sodium bicarbonate, brine and then organic layer dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain liquid which was purified on silica gel column chromatography using mixture of hexane and ethyl acetate (9:1 to 6:4), provided sweet and pleasant smelling viscous liquid. 64% yield; 1H NMR (CDCl3) δ 6.90 (3H, m), 6.70 (1H, dd, J=10.90 Hz and J=17.36 Hz), 5.79 (1H, s), 5.59 (1H, d, J=17.36 Hz), 5.11 (1H, d, J=10.90 Hz), 3.83 (3H, s); 13C NMR (CDCl3) δ 146.7, 145.7, 136.7, 130.3, 120.1, 114.5, 111.4, 108.1, 55.9.

Provenance & Evidence