Water → Ethyl hydroxybiphenylcarboxylate

Participants

Reaction Steps

Under a nitrogen atmosphere, a stirred solution of 24.4 grams (0.100 mole) of crude 2-ethoxycarbonyl-3-phenylcyclohex-5-enone in 50 mL of carbon tetrachloride was cooled in an ice bath, and a solution of 16.1 grams (0.100 mole) of bromine in 50mL of acetic acid was added dropwise. Upon completion of addition, the reaction mixture was stirred at the ice-bath temperature for 30 minutes. After this time the reaction mixture was warmed to reflux where it was stirred for about 21 hours. The reaction mixture was cooled and then was stirred with 80 mL of methylene chloride and 80 mL of water. The layers were separated, and the organic layer was washed with two portions of water and with one portion of an aqueous solution saturated with sodium bicarbonate. The organic layer was dried with sodium sulfate and magnesium sulfate and then was filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 2:1-heptane and methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure to yield 7.1 grams of ethyl 6-phenylsalicylate. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence