Succinic anhydride → 4-(2,4-Dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid

HRID 1798098Notes

Reaction equation

HRID 1798098 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[CH:4]=1.[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH2:14][CH2:13]1.[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:11][O:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([CH3:9])[C:6]=1[C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 7922Succinic anhydrideHCID 14798Sodium Hydroxide2×HCID 778443,5-DimethoxytolueneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 582928204-(2,4-Dimethoxy-6-methyl-phenyl)-4-oxo-butyric acidYield 43.7%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

To a suspension of 1,3-dimethoxy-5-methyl-benzene (5.10 g, 33.55 mmol) and succinic anhydride (3.69 g, 36.91 mmol) in nitrobenzene (100 mL) was added AlCl3 (8.9 g, 67.10 mmol). The reaction mixture was stirred at room temperature for 16 hours then carefully poured into aqueous NaOH. The pH was adjusted to 10 with solid NaOH and the aqueous solution washed with dichloromethane. The pH of the aqueous solution was adjusted to 3 with concentrated HCl and extracted with EtOAc. The organic extracts were dried and concentrated in vacuo. The residue was triturated dichloromethane to give 4-(2,4-dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid as a pale yellow solid (3.7 g, 43%). 1H NMR (400 MHz, MeOD-d4) δ 6.44 (s, 1H), 6.40 (s, 1H), 3.80 (s, 3H), 3.78 (s, 3H), 3.03 (t, J=8.1 Hz, 2H), 2.60 (t, J=8.1 Hz, 2H), 2.19 (s, 3H).

Workup

  1. washthe aqueous solution washed with dichloromethane
  2. extractionextracted with EtOAc
  3. customThe organic extracts were dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated dichloromethane

Sources & evidence

ORD record
ord-0ff1c21556ea45c4b48bdc90d42c1f45
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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