Succinic anhydride → 3-(2,4-Dimethylbenzoyl)Propionic Acid

Reaction equation

[C:1]1([CH3:8])[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[CH:2]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH2:11][CH2:10]1.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH3:8][C:1]1[CH:2]=[C:3]([CH3:7])[CH:4]=[CH:5][C:6]=1[C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:15]

Participants

Reactant 3

HCID 7922Succinic anhydride

HCID 7929M-Xylene

HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2945333-(2,4-Dimethylbenzoyl)Propionic AcidYield 92%

Procedure

m-Xylene 10f (98%, 5.5 eq) was reacted with succinic anhydride (99%, 1 eq) and AlCl3 (95%, 2 eq) for 42 h according to the general procedure. Extractive purification of the crude product afforded white crystals of 11f were obtained in 92% yield. 1H-NMR: 7.66 (d, 1H, Ar--H); 7.07 (d, 2H, Ar--H); 3.22 (t, 2H, CH2CH2COOH); 2.77 (CH2CH2COOH); 2.49 (s, 3H, CH3); 2.35 (s, 3H, CH3).