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

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

Run No	Solvent	Bp^b(°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	C₆H₅Cl^c	131	58.6	100	----	----
11	CS₂	46	55.4	100	----	----
12	CH₃NO₂^d	101	11.8	100	----	----
13	C₆H₅NO₂^d	211	Trace	Trace	----	----
14	ClCH₂CH₂Cl^e	84	99.9	1.6	43.3	55.1
15	ClCH₂CH₂Cl^f	84	92.4	----	37.6	62.4

^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.

ISSN: 2661-801X