Styrene → Styrene

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,100 grams (g) of anhydrous phenylcyclohexane, 40 g of metallic sodium and 11 g of isopropyl alcohol was placed in a 5-liter glass flask and heated to 130° C., and 650 g of styrene was dropped over 3 hours while vigorously stirring and subsequently the resulting mixture was stirred for 1 hour to complete the reaction. Stirring was stopped and the reaction mixture was allowed to stand and cool. Then an oil layer was separated and 200 g of ethanol was added. The resulting mixture was washed three times with each of 2 liters (l) of a 5N aqueous solution of hydrochloric acid and 2 l of saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The unreacted phenylcyclohexane was distilled away by the use of a rotary evaporater, and the residue was distilled under reduced pressure to yield 850 g of a fraction having a boiling point of 160°-170° C. at 0.3 mmHg (this fraction is hereinafter referred to as "Fraction f-1") and 550 g of a fraction having a boiling point of 210°-220° C. at 0.3 mmHg (this fraction is hereinafter referred to as "Fraction f-2"). An analysis confirmed that the Fraction f-1 was a compound resulting from addition of one styrene molecule to phenylcyclohexane, i.e., 1-phenyl-1-(2-phenylethyl)cyclohexane, and the Fraction f-2 was a compound resulting from addition of two styrene molecules to phenylcyclohexane, i.e., 1-phenyl-1-(2,4-diphenylbutyl)cyclohexane.

Provenance & Evidence