p-Toluenesulfonic acid → HCID 70633993, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 50 g of m-acetoxy-acetylacetanilide, 1 g of p-toluene sulfonic acid and 50 ml of methyl orthoformate was stirred for 16 hours at 20°C. and after the addition of 2 ml of quinoline and 200 ml of toluene, the reaction mixture was heated at 140°C. for 4 hours while distilling off a toluene-methanol azeotrope. The mixture was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. The product was eluted with an 8-2 methylene chloride-acetone mixture and was crystallized from isopropyl ether to obtain 29.5 g of m-acetoxy-3-methoxy-crotonanilide melting at 111°C.

Provenance & Evidence