Sodium Hydroxide → 8-Bromo-2-methoxy-1-methyl-11,12-dihydro-6H-dibenzo[a,e]cycloocten-5-one

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Reaction Conditions

Reaction Steps

To a stirred suspension of 5-bromo-2-[2-(3-methoxy-2-methyl-phenyl)-ethyl]-phenylacetic acid (11) (4.38 g; 12.06 mmol) in toluene (20 mL), was added phosphorous pentoxide (6.0 g; 42.2 mmol). The mixture was heated at 90° C. for 16 hours. The mixture was cooled, treated with 1.0 N solution of sodium hydroxide and extracted with chloroform. The extracts were combined, dried over Na2SO4, and evaporated. The resultant residue was chromatograped on silica gel using hexane and ethyl acetate (4:1) to give compound 12 as colorless crystals, 2.40 g; 55% yield.

Provenance & Evidence