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Table 2 Results from Friedel-Crafts acetylation of 3,3′-dimethylbiphenyl in the boiling reaction mixture using the Perrier addition procedure a

From: A reactivity-selectivity study of the Friedel-Crafts acetylation of 3,3′-dimethylbiphenyl and the oxidation of the acetyl derivatives

Run No Solvent Bpb(°C) Yield (%) Isomer distribution (%)
     4-Ac 4,4′-diAc 4,6′-diAc
7 CH2Cl2 40 68.9 100 ---- ----
8 ClCH2CH2Cl 84 96.5 100 ---- ----
9 Cl2CHCHCl2 147 68.2 100 ---- ----
10 C6H5Clc 131 58.6 100 ---- ----
11 CS2 46 55.4 100 ---- ----
12 CH3NO2d 101 11.8 100 ---- ----
13 C6H5NO2d 211 Trace Trace ---- ----
14 ClCH2CH2Cle 84 99.9 1.6 43.3 55.1
15 ClCH2CH2Clf 84 92.4 ---- 37.6 62.4
  1. a The 3,3′-dmbp:AcCl:AlCl3 molar ratio was 1:1:1 unless otherwise stated and the reaction time was 23 h. b Boiling point of the neat solvent. c In addition 4-chloroacetophenone was formed in ~20% yield. d The major products were dark colored polymeric materials and other unidentified compounds. e The 3,3′-dmbp:AcCl:AlCl3 molar ratio was 1:4:4. fThe 3,3′-dmbp:AcCl:AlCl3 molar ratio was 1:6:6.