o-, m- and p-t-Butyltoluenes

Abstract

March, 1949 0-, m-AND P-t-BUTYLTOLUENES 873

CONDENSATIONS BY SODIUM. XXXVIII. THE METALATION OF tert-BUTYLBENZENE BY AMYLSODIUM AND THE EFFECTS OF ASSOCIATED SALTS1, 2

“…178.0 (Calc'd 178.2). The para isomer melted at 167.0°[ reported (18) 165.0-165.6°] and had N.E. 178.5.…”

Kinetics of the Reaction of Representative Benzyl Halides with Aromatic Compounds; Evidence for a Displacement Mechanism in the Friedel—Crafts Reactions of Primary Halides1,2

“…Finally, it is apparent that this mechanism accounts for the formation of 40-60% re-propylbenzene in the alkylation of benzene with re-propyl halides. 6 Presumably the formation of 60-40% of the isopropyl derivative arises from the concurrent isomerization of the re-propyl halide. It is known that the isomerization occurs under the conditions required for the alkylation.11 In the alkylation of benzene with re-propyl alcohol and benzene, the formation of only the normal alkyl derivative is reported.6 It is probable that under the reaction conditions re-propyl alcohol is not isomerized into the isopropyl derivative as readily as the corresponding halide.…”

The Friedel and Crafts Reaction in Qualitative Organic Chemistry. Ii. Aroyl Propionic Acids of Aromatic Hydrocarbons

“…After acidification with 6 N HC1, the precipitate was washed with cold water and was recrystallized from dilute alcohol. The melting point of the substituted benzoic acid obtained was 166-167.5°, while the recorded melting point of -ferí-butylbenzoic acid is 165-165.6° ( 19).…”