US EPA

978970 

Journal Article 

Friedel-Crafts alkylation of benzene with 1,2-diphenyl-2-propanol, 1-chloro-2,3-diphenylpropane and 2-methyl-1-phenyl-2-butanol 

Khalaf, AA; Awad, IM; El-Emary, TI; Abd E-Aal, HAK 

2010 

Yes 

Journal of the Indian Chemical Society
ISSN: 0019-4522 

87 

5 

595-600 

English 

WOS:000278925800009 

The alkylation of benzene with 1,2-diphenyl-2-propanol (1) using AlCl(3)/CH(3)NO(2) catalyst gave a mixture of 1,2,2- (4) and 1,1,2-triphenylpropane (5) as product alkylates. With 85% H(2)SO(4) catalyst, the product consisted of E-1,2-diphenylpropene (6) after 2 h of a mixture of 5 and 6 after 18 h. Similar alkylation of benzene with 1-chloro-2,3-diphenylpropane (2) using AlCl(3) catalyst gave a mixture consisting of 4, 5 and 6. Finally, alkylation of benzene with 2-methyl-1-phenyl-2-butanol (3) using AlCl(3)/CH(3)NO(2) gave 2-methyl-1,1-diphenylbutane (10) as sole product alkylate. The identities of the products were confirmed spectroscopically and by comparison with unequivocally prepared samples. Mechanisms are proposed to rationalise the observed results. 

Friedel-Crafts alkylation; triphenylpropanes; carbocation rearrangement; dimerisation