Acetone → Methyl p-ethoxycinnamate

Participants

Reaction Steps

This ester was treated with excess ethyl iodide in the presence of potassium carbonate in refluxing dry acetone for 48 hours. A moderate yield of methyl p-ethoxycinnamate was obtained as white crystals from methanol, mp 68--70° C: λmaxCCl4 5.8, 6.09, 6.22, 6.6, 8.0, 8.56, 9.53, 10.15, and 10.8 μ. Reduction of methyl p-ethoxycinnamate in benzene with LAH gave a 50% yield, after recrystallization from methanol, of p-ethoxycinnamyl alcohol, mp 85° C: λmaxCC14 2.75, 6.2, 6.61, 6.75, 8.93, 9.2, 9.55, 9.97, 10.3, 10.85, and 11.87 μ.

Provenance & Evidence