Hydrochloric Acid → HCID 9794980, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-acetoxy-3-methyl-1-(naphth-1-yl)butan-1-one (8.4 g), IMS (200 ml) and hydrochloric acid (1M; 100 ml) were boiled under reflux for 4 hours. The mixture was cooled, evaporated in vacuo and partitioned between dichloromethane and brine. The organic layer was separated, dried with sodium sulphate, filtered and evaporated in vacuo to afford a mixture of crude 2-hydroxy-3-methyl-1-naphthalen-1-yl-butan-1-one and 1-hydroxy-3-methyl-1-naphthalen-1-yl-butan-2-one (F) (7.4 g). Cyanamide (1.3 g) and anhydrous ethanol (50 ml) were added and the resulting mixture was boiled under reflux for 96 hours. After cooling the volatiles were removed in vacuo and the residue heated at 115° C. for a further 48 hours. The mixture was cooled, triturated with chloroform (80 ml) and filtered. The filtrate was washed with water, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (7) was obtained (0.26 g; m.p. 127-129° C.) following silica gel column chromatography of the residue in 33% ethyl acetate in petroleum ether and re-crystallisation from dichloromethane/petroleum ether.

Provenance & Evidence