Succinic anhydride → 4-(2,4-Dimethylphenyl)-4-oxobutanoic acid

HRID 260177Notes

Reaction equation

HRID 260177 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

4

Reactant 3

HCID 7922Succinic anhydrideHCID 7929M-XyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2945334-(2,4-Dimethylphenyl)-4-oxobutanoic 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).

Workup

  1. customExtractive purification of the crude product

Sources & evidence

ORD record
ord-df056c4e49d144f7b111206357692e7c
Source dataset
uspto-grants-1996_06
Patent number
US05525736

Reaction notes

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