Toluene → tert-Octylamine

Participants

Reaction Steps

2.0 Parts of 5-(3-t-butyl-2-hydroxy-5-methyl-phenyl)-5-methylhexanoic acid and 2.0 parts thionyl chloride in 25 parts of toluene were stored for 2 hours at room temperature. The toluene and other volatiles were then stripped off at room temperature and 16 mb pressure. To the residue was then added 10 parts of 1,1,3,3-tetramethyl-butylamine and this mixture heated for 3 hours on a steam-bath. After diluting the reaction mixture with ether, the ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium hydroxide, and water. Evaporation of the ether and crystallisation from 60°-80° C. petroleum-ether gave 5-(3-t-butyl-2-hydroxy-5-methylphenyl)-5-methyl-hexanoic acid amide of 1,1,3,3-tetramethylbutylamine m.p. 110°-2° C. with the following percentage composition by weight.

Provenance & Evidence