Dichloromethane → 1,1-Bis (3-chloro-4-hydroxyphenyl)cyclododecane

Participants

Reaction Steps

To a slurry containing 10 grams (0.0284 mole) of 1,1-bis(4-hydroxyphenyl)cyclododecane, prepared substantially in accordance with the procedure of Example 1, and 50 milliliters of methylene chloride, there is slowly added, at a temperature of 25°-27° C. and with stirring, a solution containing 26 grams (0.19 mole) of sulfuryl chloride and 20 milliliters of methylene chloride. During the addition of this solution the slurry turns to a solution. The reaction is followed by gas chromatographic analysis of samples removed from the reaction mixture. When analysis of these samples indicates the absence of the 1,1-bis(4-hydroxyphenyl)cyclododecane the solution is stripped on a rotary evaporator under water aspirator vacuum. Analysis of the solids indicates that they contain 93.6% of 1,1-bis(3-chloro-4-hydroxyphenyl)cyclododecane; 6% of 1-(4-hydroxyphenyl), 1-(3-chloro - 4-hydroxyphenyl)cyclododecane; and 0.4% of 1-(3-chloro-4-hydroxyphenyl),1-(3,5-dichloro-4-hydroxyphenyl)cyclododecane. The solids are recrystallized from methanol to yield the pure 1,1 -bis (3-chloro-4-hydroxyphenyl)cyclododecane, which has a melting point of 167°-169° C. and a gas chromatographic retention time of 28.04 minutes relative to 13.97 minutes for p-cumyl phenol.

Provenance & Evidence