Methyl iodide → Phenylpropynoic acid methyl ester

Participants

Reaction Steps

Typical Procedure for Methylation of Propiolic Acid with Iodomethane (1b as Example) CH3I (2.2 mmol) and K2CO3 (2.2 mmol) were added to the solution of Propiolic acid (1b, 2 mmol) in acetonitrile and the obtained mixture was stirred at room temperature. The reaction was monitored by TLC until the starting 1b disappeared. After 3 hours, the mixture was extracted with ether (3×5 mL). The combined ether part was purified by column chromatography on silica gel (dichloromethane:hexane=1:3) to give pure methyl 3-phenylpropiolate in 98% yield. GC/Ms: m/z: 160. Data for 1H and 13C NMR of methyl 3-phenylpropiolate was conducted in CDCl3 and consistent with the data in reported literature.

Provenance & Evidence