Acetic Acid → Ferulic Acid

Participants

Reaction Steps

A mixture of vanillin (2.50 g, 0.0164 mol), malonic acid (3.41 g; 0.0328 mol), piperidine (3–5 mL) and acetic acid (10–20 mL) were taken in a round bottom flask and the reaction mixture was refluxed for 5–6 hours instead of microwave irradiation as mentioned in Example I. The cooled mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with dil HCl., saturated sodium chloride and then organic layer dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain solid which was recrytallised with mixture of methanol and hexane, provided ferulic acid as a solid compound mp 169° C. (lit mp 168–171° C.) in 65% yield; 1H NMR (DMSO-d6) δ 12.13 (1H, s, COOH), 7.48 (1H, d, Ar—CH═CH—COOH), 7.27 (1H, s, H-3), 7.07 (1H, d, H-6), 6.78 (1H, d, H-5), 6.36 (1H, d, —CH═CH—COOH), 3.81 (3H, s, 2-OCH3); δ168.9 (COOH), 149.8 (C-1), 148.7 (C-2), 145.4 (CH═CH—COOH), 126.6 (C-4), 123.7 (C-5), 116.4 (C-3 & C-6), 111.8 (CH═CH—COOH), 56.4 (2-OCH3).

Provenance & Evidence