Hydroxyacetone → 3-Methyl-6,7-dihydro-1-benzofuran-4(5H)-one

Participants

Reaction Steps

A mixture of 1,3-cyclohexanedione (3.36 g, 30 mmol), acetol (hydroxyacetone; 2.22 g, 30 mmol), and zinc chloride (4.09 g, 30 mmol) in ethanol (10 mL) was heated at reflux temperature for 3 hours. After cooling, the mixture was dissolved in ethyl acetate (100 mL). The whole was washed with water (100 mL), brine (100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chlomatography eluting with ethyl acetate - hexane (1:10) to give the subtitle compound (1.69 g, 38% yield).

Provenance & Evidence