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

HRID 2393220Notes

Reaction equation

HRID 2393220 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 is available from 4-chloro-o-xylene by Friedel-Crafts acylation with oxalyl chloride to give 2,2'-dichloro-4,4',5,5',-tetramethylbenzophenone, 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-77aea4ef9bbd4d37990579816b14e257
Source dataset
uspto-grants-1998_09
Patent number
US05807498

Reaction notes

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