Methacrolein → Ethyl 5-methylsalicylate

Participants

Reaction Steps

A stirred mixture of 2-methylacrolein (22.8 g, 92%, 0.30 mol), ethyl 2-chloroacetoacetate (41.1 g, 95%, 0.25 mol) and anhydrous sodium acetate (24.6 g, 0.30 mol) in acetic acid is heated at reflux temperature under N2 for 16 hr., cooled to room temperature and concentrated in vacuo to give a residue. The residue is partitioned between ethyl acetate and water. The organic phase is concentrated in vacuo to give the title product as an oil, 44.2 g, 71.9% purity (70.6% yield), characterized by NMR analysis).

Provenance & Evidence