Water → P-Cresol

Participants

Reaction Steps

Four grams of chlorine was bubbled through a stirred solution of 10.8 g of p-cresol (10 mmoles) in 100 ml of carbon tetrachloride for about 30 minutes. A five-gram sample, removed and analyzed and showed 46.9% p-cresol and 53.1% 2-chloro-p-cresol. Then 0.1 ml of ethanol and 10.00 g powdered anhydrous calcium bromide were added to the chlorinated p-cresol mixture. The mixture was stirred in the absence of atmospheric moisture for about 16 hours. A washed-and-dried solid was obtained weighing 10.40 g. A sample of the solid was hydrolyzed by water and extracted five times with carbon tetrachloride. GC analysis of the combined extract gave 96.6% p-cresol and 3.3% 2-chloro-p-cresol, showing substantially complete separation of p-cresol from its chlorinated derivative by complexation with calcium bromide.

Provenance & Evidence