Succinic anhydride → 4-Oxo-4-(2,4,6-trimethylphenyl)butanoic acid

HRID 260179Notes

Reaction equation

HRID 260179 reaction equation
[C:1]1([CH3:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH3:9][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:10]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:16]

Participants

4

Reactant 3

HCID 7922Succinic anhydrideHCID 7947MesityleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3461804-Oxo-4-(2,4,6-trimethylphenyl)butanoic acidYield 54%

Procedure

Mesitylene 10i (99%, 4.8 eq) was reacted with succinic anhydride (99%, 1 eq) and AlCl3 (95%, 2 eq) for 72 h according to the general procedure. Extractive purification of the crude product afforded white crystals of 11i in 54% yield. 1H-NMR (DMSO-d6): 6.63 (s, 2H, Ar--H); 2.84 (t, 2H, CH2CH2COOH); 2.22 (s, 3H, p-CH3); 2.18 (t, 2H, CH2CH2COOH); 2.13 (s, 6H, o-CH3).

Workup

  1. customExtractive purification of the crude product

Sources & evidence

ORD record
ord-8afe87d178e6471fbe0eaf4d50f27741
Source dataset
uspto-grants-1996_06
Patent number
US05525736

Reaction notes

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