4-Chloro-o-xylene → 2,2'-Dichloro-4,4',5,5'-tetramethylbenzophenone

HRID 2931

Reaction equation

HRID 2931 reaction equation
[CH:1]1[C:6]([C:7](C2C=CC3C(OC(=O)C=3C=2)=O)=[O:8])=[CH:5][C:4]2[C:20](O[C:23](=O)[C:3]=2[CH:2]=1)=O.[Cl:25][C:26]1[CH:27]=[C:28]([CH3:33])[C:29]([CH3:32])=[CH:30][CH:31]=1.C(Cl)(=O)C([Cl:37])=O>>[Cl:25][C:26]1[CH:27]=[C:28]([CH3:33])[C:29]([CH3:32])=[CH:30][C:31]=1[C:7]([C:6]1[CH:5]=[C:4]([CH3:20])[C:3]([CH3:23])=[CH:2][C:1]=1[Cl:37])=[O:8]

Participants

4

Reactant 3

HCID 328864-Chloro-o-xyleneHCID 65578Oxalyl chlorideHCID 754984,4'-Carbonyldiphthalic anhydride

Product 1

HCID 150271722,2'-Dichloro-4,4',5,5'-tetramethylbenzophenone

Procedure

Specific benzophenonetetracarboxylic dianhydrides preferred in this invention are readily available from commercial sources or synthesis. For instance, 3,3',4,4'-benzophenonetetracarboxylic dianhydride (D1) is available from Aldrich Chemical Co., Inc. (1001 W. St. Paul Ave., Milwaukee, Wis. 53233). 2,2'-Dichloro-4,4',5,5'-benzophenone tetracarboxylic dianhydride (D2) is available from 4-chloro-o-xylene by Friedel-Crafts acylation with oxalyl chloride to give 2,2'dichloro-4,4',5,5',-tetramehtylbenzophenone, followed by oxidation with nitric acid and dehydration of the resulting tetracarboxylic acid as described by Falcigno, et al., J. Poly. Sci. 1992, 30, 1433.

Workup

  1. customare readily available from commercial sources or synthesis

Sources & evidence

ORD record
ord-9d4147d3edea46ffb150787b3152cac8
Source dataset
uspto-grants-1998_03
Patent number
US05731405

Linked notes

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