Hydrochloric Acid → HCID 19022457, compound

Participants

Reaction Steps

A solution of 5.21 grams (12.8 mmol.) of 2,2-bis(4-methoxybiphenylyl) propane and 6.30 grams (25.5 mmol.) of boron tribromide in 150 ml. of methylene chloride was stirred at room temperature in a nitrogen atmosphere for 18 hours, after which 50 ml. of 10% aqueous sodium hydroxide solution was cautiously added to hydrolyze boron compounds. After 1/2 hour, the mixture was diluted with an equal volume of ethyl acetate and acidified by the addition of 10% aqueous hydrochloric acid solution. The organic phase was separated, dried over magnesium sulfate and concentrated to give the crude product as yellow flakes. It was eluted through a plug of silica gel and recrystallized from chlorobenzene, to give a crude yield of 2.58 grams (53% of theoretical) of the desired 2,2-bis(4-hydroxybiphenylyl) propane as light tan crystals. Residual color was removed by refluxing for 48 hours in a solution of 2 grams of potassium hydroxide in 30 ml. each of tetrahydrofuran and methanol, followed by flash chromatography over silica gel with a mixture of ethyl acetate and hexane, to give fine white needles with a melting point of 237°-239° C.

Provenance & Evidence