HALOGENATION. X. CHLORIC ACID AS A REAGENT IN ORGANIC CHEMISTRY

Rasik Lal Datta, Jogendra Kumar Choudhury
1916 Journal of the American Chemical Society  
I079 The yield was 93% of the theoretical. The percentage of bromine formed was 40.14; the theoretical percentage is 40.61. Glycol.-Ten grams of the alcohol were heated 2 hours with 145 g. of constant-boiling hydrochloric acid (molecular ratio I : 5). The mixture was then fractionated; neither ethylene chloride nor the chlorohydrin were obtained.' Twenty grams of glycol were boiled for 2 hours with 165 g. of hydrobromic acid (molecular ratio I : 3). The mixture was then fractionated, using a
more » ... ionated, using a GIinsky tube. No bromohydrin was obtained, but there were formed 8 cc. of an insoluble oil which proved to be ethylene bromide, the yield being 36% of the theoretical. In another experiment when the mixture was heated for a shorter time, some of the bromohydrin was obtained. The exact conditions which determine replacement of one and two hydroxyl groups by bromine were not determined. Glycerol.-A mixture of IO g. of glycerol and 55 g. of hydrobromic acid (molecular ratio I : 3 ) was distilled slowly a t ordinary pressure until the temperature of the vapor was 140'. The distillation was continued a t 33 mm. pressure. The product obtained boiled at 146-175'. After three fractionations at 30 mm. pressure 6 g. of an oil which boiled at 145-147 O (corrected) were obtained. The bromohydrins have not been carefully studied. It is probable that the compound obtained was identical with that described by Veley,' who prepared it by passing hydrogen bromide into glycerol. The boiling point recorded is 160' a t 66 mm. NASHVILLE, TBNN
doi:10.1021/ja02262a015 fatcat:z2p54txgxrco3ab6rq4tyt3jte