Toluene → 4-(4-Methylphenyl)-4-oxobutanoic acid

Reaction equation

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

Participants

Reactant 3

HCID 1140Toluene

HCID 7922Succinic anhydride

HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2441624-(4-Methylphenyl)-4-oxobutanoic acidYield 75%

Procedure

Toluene 10b (99.9%, 5.5 eq) was reacted with succinic anhydride (99%, 1 eq) and AlCl3 (95%, 2 eq) for 24 h according to the general procedure. Yellow crystals of 11b were obtained in 75% yield. 1H-NMR: 7.88 (d, 2H, J=8.2 Hz, Ar--H); 7.26 (d, 2H, J=4.8 Hz, Ar--H); 3.29 (t, 2H, J=6.6 Hz, CH2CH2COOH); 2.80 (t, 2H, J=6.6 Hz, CH2CH2COOH); 2.41 (s, 3H, CH3). 13C-NMR: 192.44; 178.70; 144.13; 133.91; 129.29; 128.14; 33.02; 28.06; 21.63.

Sources & evidence

ORD record: ord-eedb300dd053411aa31b470247cd67c7
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05525736

Reaction notes

Loading…