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

HRID 1892091Notes

Reaction equation

HRID 1892091 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH2:7][CH2:6]1.[C:12]1([CH:18]([CH3:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCCl.Cl>[CH:18]([C:12]1[CH:17]=[CH:16][C:15]([C:5](=[O:11])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:14][CH:13]=1)([CH3:20])[CH3:19]

Participants

6

Reactant 3

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

Product 1

HCID 96145Benzenebutanoic acid, 4-(1-methylethyl)-gamma-oxo-Yield 84.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of aluminum (III) chloride (6.7 g, 50.1 mmol) and succinic anhydride (2 g, 20 mmol) in 1,2-dichloroethane was added Cumene (2 g, 16.7 mmol) at 0-5° C. The reaction mixture was stirred at ambient temperature for 16 hours, diluted with 20 mL of aqueous HCl solution (1 M) and extracted with ethyl acetate (3×80 mL). The combined organic phases were washed with saturated sodium chloride (100 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica-gel (4×20 cm, petroleum ether:ethyl acetate=8:1 elution) to give 3.1 g of compound 76. 1H NMR (CDCl3, 300 MHz) δ 1.27-1.29 (d, 6H), 2.80-2.84 (t, 2H), 2.95-3.00 (m, 1H), 3.29-3.33 (t, 2H), 7.32-7.34 (d, 2H), 7.92-7.94 (d, 2H). MS m/z 221 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×80 mL)
  2. washThe combined organic phases were washed with saturated sodium chloride (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica-gel (4×20 cm, petroleum ether:ethyl acetate=8:1 elution)

Sources & evidence

ORD record
ord-ea3023cacdf44ee9805e14f9f01acef9
Source dataset
uspto-grants-2013_08
Patent number
US08507647B2

Reaction notes

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