Hydrochloric Acid → HCID 22324850, compound

Participants

Reaction Steps

A solution of 12.51 g (61.93 mmol) of 3,4-dihydro-6-(2-propenyloxy)-1(2H)-naphthalenone in 125 mL of N,N-diethylaniline was stirred and heated in a 225°-230° C. oil bath, for 20.5 hr. The resulting dark-amber solution was cooled and poured into 300 mL of cold 3N HCl. The mixture was worked-up with ether in the usual manner giving 12.29 g of a yellow solid which was a mixture of the 5- and 7-allyl isomeric hydroxy naphthalenones. This material was recrystallized from ethyl acetate giving the pure 5-allyl isomer in 60% yield, in several crops. The analytical specimen was a yellow solid, mp 145°-148° C.

Provenance & Evidence