Arylalkylation of 4-tert-butyltoluene with substituted benzyl chlorides

Journal Article · Fri Aug 01 04:00:00 EDT 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6952849

Pozdnyakovich, Y V; Savyak, R P; Shein, S M

The reaction of 4-alkylbenzyl chlorides with 4-tert-butyltoluene in the presence of titanium tetrachloride and ferric chloride leads to the formation of 2-methyl-4'-alkyl-5-tert-butyldiphenylmethanes. The arylalkylation of 4-tert-butyltoluene with 2- and 4-chlorobenzyl chlorides, catalyzed by titanium tetrachloride, leads to the formation of mixtures of 2-methyl-5-tert-butyldiphenylmethane, 2-tert-butyl-5-methyldiphenylmethane, and isomeric methyldiphenylmethanes containing a chloride atom in the benzyl fragment. The products of the reaction catalyzed by ferric chloride do not contain 2-tert-butyl-5-methylchlorodiphenylmethanes. The reaction of 4-nitrobenzyl chloride with 4-tert-butyltoluence in the presence of ferric chloride leads to the formation of a mixture of 2-methyl-4'-nitro-5-tert-butyldiphenylmethane and isomeric methylnitrodiphenylmethanes. Under the influence of AlCl/sub 3/-CH/sub 3/NO/sub 2/ in benzene 2,4'-dimethyl-5-tert-butyldiphenylmethane eliminates both the 4-methylbenzyl group and the tert-butyl group. Under analogous conditions 2-methyl-5-tert-butyldiphenylmethanes containing a chlorine atom or a nitro group in the benzyl fragment are dealkylated with the elimination of only the tert-butyl group.

• Research Organization: Robezhnoe Branch, Sci-Res Institute of Organic Intermediates
• OSTI ID: 6952849
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 22:3,PT.2; ISSN JOCYA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKANES
ALKYLATED AROMATICS
ALKYLATION
ALUMINIUM CHLORIDES
ALUMINIUM COMPOUNDS
AROMATICS
BENZENE
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
DIAGRAMS
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
IRON CHLORIDES
IRON COMPOUNDS
KINETICS
METHANE
NITRO COMPOUNDS
NITROBENZENE
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
QUANTITY RATIO
REACTION KINETICS
TITANIUM CHLORIDES
TITANIUM COMPOUNDS
TOLUENE
TRANSITION ELEMENT COMPOUNDS
YIELDS