Dimethylformamide → Methyl cis-2-methoxy-5-methylcinnamate

Participants

Reaction Steps

A stirred solution of 6.0 g (37.46 mmol) of 6-methylcoumarin in 100 ml of dimethylformamide was treated with 3.29 g (82.41 mmol) of sodium hydroxide in 10 ml of water. After 15 minutes, 26.6 g (187.3 mmol) of methyl iodide was added. After an additional 6 hours, ether extraction provided the title compound as an oil. NMR in CDCl3 (δ units): 2.28 (singlet, 3); 3.66 (singlet, 3); 3.79 (singlet, 3); 5.97 and 7.13 (doublet, J=12 Hz, 1); 6.76 (doublet, J=8 Hz, 1); 7.09 (broad doublet, 1); 7.35 (broad singlet, 1).

Provenance & Evidence