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

HRID 260178Notes

Reaction equation

HRID 260178 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12]1.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][C:8]=1[C:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:17]

Participants

4

Reactant 3

HCID 7922Succinic anhydrideHCID 90251,3-DimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2381964-(2,4-dimethoxyphenyl)-4-oxobutanoic acidYield 68%

Procedure

1,3-Dimethoxybenzene 10 h (99%, 6 eq) was reacted with succinic anhydride (99%, 1 eq) and AlCl3 (95%, 2 eq) for 19 h according to the general procedure. Recrystallization in EtOH gave white crystals of 11 h in 68% yield. 1H-NMR: 7.89 (d, 1H, J=8.7 Hz, Ar--H; 6.55 (dd, 1H, J=8.7 and 2.3 Hz, Ar--H); 6.46 (d, 1H, J=2.3 Hz, Ar--H); 3.91 (s, 3H, OCH3); 3.86 (s, 3H, OCH3); 3.30 (t, 2H, J=6.6 Hz, CH2CH2COOH); 2.73(t, 2H, J=6.6 Hz, CH2CH2COOH). 13C-NMR: 197.62; 164.79; 161.23; 132.96; 105.29; 98.31; 55.54; 55.47; 38.42; 28.67.

Workup

  1. customRecrystallization in EtOH
  2. customgave white crystals of 11 h in 68% yield

Sources & evidence

ORD record
ord-418ad72964a54621adeefe06955f1b9c
Source dataset
uspto-grants-1996_06
Patent number
US05525736

Reaction notes

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