Oxalyl chloride → HCID 22750665, compound

Participants

Reaction Steps

25 g. of 1-carboxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one in 250 ml. of benzene are heated with 20 g. of oxalyl chloride for 2 hours at reflux and subsequently concentrated under reduced pressure. The resulting crystalline 1-chlorocarbonyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one is dissolved in 200 ml. of benzene and then it is added dropwise to a solution of the magnesium salt of diethyl malonate (about 50 g. in 500 ml. of ether) over a period of about 5 minutes and heated at reflux for 12 hours. Subsequently, the reaction mixture is divided between ether and dilute sulfuric acid, washed with water, sodium bicarbonate solution and water, dried and evaporated. The residue is heated in 30 ml. of ethyl acetate, 20 ml. of water and 3.7 ml. of concentrated sulfuric acid at reflux for 15 hours. Then, it is poured over ice water and extracted with ether. The ethereal extract is washed with water, sodium bicarbonate solution and water, dried and evaporated, whereby 1-acetyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one having a melting point of 65°-68° C. is obtained.

Provenance & Evidence