Cumene → Benzenebutanoic acid, 4-(1-methylethyl)-gamma-oxo-

HRID 260175Notes

Reaction equation

HRID 260175 reaction equation
[C:1]1([CH:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH:7]([C:1]1[CH:6]=[CH:5][C:4]([C:10]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:16])=[CH:3][CH:2]=1)([CH3:9])[CH3:8]

Participants

4

Reactant 3

HCID 7406CumeneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 96145Benzenebutanoic acid, 4-(1-methylethyl)-gamma-oxo-Yield 83%

Procedure

Cumene 10d (99%, 4.8eq) was reacted with succinic anhydride (99%, 1 eq) and AlCl3 (95%, 2 eq) for 120 h according to the general procedure. Extractive purification of the crude product afforded white crystals of 11d were obtained in 83% yield. 1H-NMR: 7.92 (d, 2H, Ar--H); 7.32 (d, 2H, Ar--H); 3.30 (t, 2H, CH2CH2COOH); 2.97 (sept., 1H,CH(CH3)2); 2.81 (t, 2H, CH2CH2COOH); 1.27 (d, 6H, CH(CH3)2).

Workup

  1. customExtractive purification of the crude product

Sources & evidence

ORD record
ord-c5bd26d9de804e89848d1c3620659fac
Source dataset
uspto-grants-1996_06
Patent number
US05525736

Reaction notes

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