Glutaric anhydride → 5-(4-Methoxyphenyl)-5-oxopentanoic acid

HRID 1881036Notes

Reaction equation

HRID 1881036 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[C:13]([O:16][CH2:17][CH3:18])(=O)C>C1(OC)C=CC=CC=1>[CH3:13][O:16][C:17]1[CH:18]=[CH:4][C:3]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])=[CH:2][CH:1]=1

Participants

5

Reactant 3

HCID 7940Glutaric anhydrideHCID 8857Ethyl AcetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2668175-(4-Methoxyphenyl)-5-oxopentanoic acidYield 59%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Glutaric anhydride (10.0 g) was dissolved in anisole (100 mL), aluminum chloride (25.7 g) was added, then stirred for three hours on ice. Ethyl acetate (300 mL) was added to the reaction solution, and the organic layer was washed with water (100 mL) and a saturated sodium chloride solution (100 mL). After drying on anhydrous sodium sulfate, filtration and vacuum condensation, the residue was washed with n-hexane to give the above-identified compound (11.5 g, yield 59%) as a colorless solid.

Workup

  1. washthe organic layer was washed with water (100 mL)
  2. dry with materialAfter drying on anhydrous sodium sulfate, filtration and vacuum condensation
  3. washthe residue was washed with n-hexane

Sources & evidence

ORD record
ord-97cb2635ef024ad69aafba46ea483cc4
Source dataset
uspto-grants-2012_11
Patent number
US08318781B2

Reaction notes

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