Condensation of Tertiary Aliphatic Alcohols with Aromatic Compounds in the Presence of Aluminum Chloride. IV. Tertiary Dimethyl Amyl Carbinols with Phenol

Abstract

The relative densities of solutions of methyl alcohol and toluene have been measured over the entire concentration range at -21.1, 0.0, 25.0 and 49.7°.The volume changes attending mutual solution of the two liquids have been calculated from these densities and the volume changes at a temperature near the boiling point have been estimated by extrapolation.-Suggestions have been offered as to the nature of the association, dissociation and solvation effects which may be responsible for the observed behavior.

Condensation of Dimethylamyl Carbinols With Benzene in the Presence of Aluminum Chloride

“…In the present investigation all but one of the possible amyldimethylphenylmethanes were converted into the p-hydroxy derivatives by nitration, reduction to the amine, and diazotization. These were proved, by mixed melting points of the -naphthylurethane, to be identical with the products formed by direct alkylation of phenol (9).…”

“…It is worthy of note that we were unable to obtain an octylbenzene from 2,3,4-trimethylpentanol-2 but were able to effect condensation of this alcohol with phenol (9).…”

“…Assignment of structure to the feri-octylbenzenes is based upon considerations outlined in an earlier publication and upon their conversion to p-ieri-octylphenols (9).…”

“…The p-nitro, p-amino, and p-hydroxy derivatives of six of the ieri-octylbenzenes have been reported (9) along with their methods of preparation and analysis.…”

“…The melting point recorded (9) for 2,3,3-trimethyl-2-p-hydroxyphenylpentane is in error and is corrected to 60-61°. Condensations in which larger quantities of reactants were used gave this phenol in yields as high as forty per cent.…”