In continuation and extension of previous work from this laboratory (1), the following tertiary dimethylamyl carbinols, viz: 2-methylheptanol-2 (2), 2,3-dimethylhexanol-2 (3), 2,4-dimethylhexanol-2 (4, 5), 2,5-dimethylhexanol-2 (6), 2-methyl-3-ethylpentanol-2 (7), 2,3,3-trimethylpentanol-2 (8), 2,3,4-trimethylpentanol-2 (9), and 2,4,4-trimethylpentanol-2 (10) were prepared and condensed with benzene.The resulting alkyl benzenes were separated from the reaction-mixtures by repeated fractionation under reduced pressure. Physical constants were determined. In cases where sufficient quantity of the alkylated product was available, it was nitrated, reduced, diazotized, and hydrolyzed to the corresponding phenol (9). In some cases, the monoacetamino derivative (11), was prepared.The alcohols were prepared as reported in a previous communication (9) with these exceptions. Some of the 2-methyl-3-ethylpentanol-2 was prepared by a modification of the Whitmore (12) procedure, by reacting the Grignard reagent of 3-bromopentane with acetyl chloride, treating the ketone with methylmagnesium bromide and finally hydrolyzing to give the tertiary alcohol; yield, 11%. A part of the 2,4,4-trimethylpentanol-2 was prepared by oxidation of di-isobutylene (13) to 2,2-dimethylpentanone-4 and subsequent reaction of this ketone with methylmagnesium bromide. This method gave a 22% yield of the carbinol based on diisobutylene. The method of Butlerow (10) gave a 46% yield based on diisobutylene. The physical constants of the alcohols were carefully determined and are included in summary in Table I.
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