Diethyl Ether → HCID 18987251, compound

Participants

Reaction Steps

To a mixture of 150 cc of tetrahydrofuran and 34 cc of a 3M solution of phenylmagnesium bromide in diethylether at 40° C. under an argon athmosphere, are added 15 g of 3,5-dichloroanisole and 5.5 g of bis(triphenylphosphine)nickel(II) chloride. The resultant black mixture is heated for 6 hours to 65° C. and then poured into 400 cc of a saturated aqueous solution of ammonium chloride. After extraction with ethyl acetate (3×150 cc), the combined organic extracts are washed with water, dried (MgSO4) and concentrated in vacuo. The resultant residue is flash chromatographed on silica gel (30-60 mm; eluent: 20:0.1 n-hexane/ethyl acetate) and recristallized from 20 cc of methanol to give 3,5-diphenyl-anisole as a white solid. (m.p.=93°-94° C.)

Provenance & Evidence