Water → 5-Methoxy-4,4-dimethyl-5-oxopentanoic acid

HRID 2268019Notes

Reaction equation

HRID 2268019 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][CH2:6][C:7]([O:9]C)=[O:8].C(=O)([O-])[O-].[K+].[K+].O1CCCC1.O>CO>[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:11])([CH3:12])[CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 830831,5-Dimethyl 2,2-dimethylpentanedioate

Product 1

HCID 134932415-Methoxy-4,4-dimethyl-5-oxopentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl-2,2-dimethylglutarate (18.26 g, 97.0 mmol) and potassium carbonate (27.14 g, 196.4 mmol) were dissolved in 280 mL of 3:2:2 methanol:tetrahydrofuran:water. The reaction mixture was stirred at ambient temperature for 73 hours, and then concentrated in vacuo. The resulting residue was taken up in water. The aqueous phase was extracted twice with ethyl acetate, and the organic phase was discarded. The aqueous phase was then acidified with a 1.0M aqueous solution of hydrochloric acid, and extracted three times with ethyl acetate. The ethyl acetate layer was washed once with brine, dried over sodium sulfate, filtered, and the filtrate was evaporated to dryness to give the title compound as an oil.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. washThe ethyl acetate layer was washed once with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-8c106cacc21741a681d93b999ada382f
Source dataset
uspto-grants-2001_12
Patent number
US06326372B1

Reaction notes

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