Phthalic Anhydride → 2-(2,5-Dimethylbenzoyl)benzoic acid

HRID 345610Notes

Reaction equation

HRID 345610 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:16][C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1>>[CH3:16][C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][C:22]=1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])=[O:5]

Participants

4

Reactant 3

HCID 6811Phthalic AnhydrideHCID 7809P-XyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2880852-(2,5-Dimethylbenzoyl)benzoic acid

Procedure

Monomers. The spirobislactone endcapping group, 4-carboxy-7,7'-dioxa-2,2'-spirobi (benzo[c]tetrahydrofuran) 5,was synthesized using a three-step procedure. Phthalic anhydride (PA) 1 was reacted with p-xylene 2 in the presence of AlCl3 to produce ##STR6## 2,5-dimethyl-2'-carboxybenzophenone 3. Oxidation by potassium permanganate yielded the triacid 4 which was cyclized to 5 by refluxing with Dowex 50X8-100 resin (H+) in 2-methoxyethyl ether and removing the water of reaction.

Sources & evidence

ORD record
ord-50dcaced812c4552b048f8a6ab489dd6
Source dataset
uspto-grants-1991_10
Patent number
US05057590

Reaction notes

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