Methanol → Methyl 3-(4-methylphenyl)-2-propenoate

Participants

Reaction Steps

A suspension of 300 g of p-methylcinnamic acid (J. Chem. Soc., Chem. Comm., 471, 1976) and 25 ml of concentrated sulfuric acid in 1.7 liters of methanol is heated to reflux for 24 hours. The solution is concentrated, cooled and filtered to give as a white solid, p-methylcinnamic acid methyl ester, mp 55°-56° C. NMR (DMSOd6) δ=7.36 (d, J=16 Hz, 1H); 7.36 (dd, J1 =30 Hz, J2 =7 Hz, 4H); 6.48 (d, J=16 Hz, 1H); 3.70 (s, 3H); 2.32 (s, 3H). IR (cm-1) 3061, 3028, 2949, 1713, 1634, 1607, 1570, 1516, 1438.

Provenance & Evidence