Sulfuric Acid → Ethane, 2-chloro-1,1-bis(p-methoxyphenyl)-

Participants

Reaction Conditions

Reaction Steps

To a 500-milliliter jacketed flask equipped with a mechanical stirrer, thermometer, and dropping funnel, and cooled to approximately 2° C. with circulating trichloroethylene thermostated cooling liquid, was charged 43.2 grams (0.40 mole) of anisole and 30.6 grams (0.20 mole) of commercial chloroacetal. To the cooled and stirred solution was added a solution of 80.0 grams (0.82 mole) of concentrated sulfuric acid dissolved in 50 milliliters of glacial acetic acid over a 1.17-hour period (1 hour and 10 minutes) at a rate sufficient to maintain the temperature at less than 15° C. When the addition was complete, the solution was stirred an additional 10 minutes, allowed to warm to 15° C. and poured into 1 liter of an ice/water mixture. The mixture was extracted with three 150-milliliter portions of diethyl ether, washed successively with three 100-milliliter portions of saturated aqueous sodium carbonate and three 100-milliliter portions of cold water, and dried over anhydrous sodium sulfate. Evaporation of the ether in vacuo yielded 55.0 grams (almost quantitative) of crude 1,1-bis(4-methoxyphenyl)-2-chloroethane as a colorless oil.

Provenance & Evidence