Hydrochloric Acid → HCID 20304544, compound

Participants

Reaction Steps

A solution of the product of step (b) (15.4 g) in ethanol (50 ml) was added to one of sodium (4.0 g) in ethanol (50 ml). To this mixture was added diethyl oxalate (50 g) and the whole mixture was heated at-reflux for 2 hours, then poured into a mixture of chloroform (500 ml) and concentrated HCl (100 ml). The organic layer was separated, evaporated to dryness and the residue was heated at reflux in ethanol (200 ml) containing concentrated hydrochloric acid (5 ml) for 2 hours. The solution was evaporated to dryness and the residue was taken up in ethyl acetate. This solution (was washed well with water, dried (MgSO4), filtered and the filtrate was evaporated to dryness leaving an oil. This was dissolved in a small amount of ethyl acetate and the solution was allowed to crystallise to give the title ester 6.3 g (30%), mp 115°-6°. It should be noted that under these reaction conditions the hydroxymethyl group of the starting naphthol has been converted into an ethoxymethyl grouping.

Provenance & Evidence