Potassium Carbonate → 5-Methoxy-4,4-dimethyl-5-oxopentanoic acid

HRID 1615815Notes

Reaction equation

HRID 1615815 reaction equation
[CH3:1][C:2]([CH3:13])([CH2:7][CH2:8][C:9]([O:11]C)=[O:10])[C:3]([O:5][CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+]>CO.C1COCC1.O>[CH3:6][O:5][C:3](=[O:4])[C:2]([CH3:1])([CH3:13])[CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 830831,5-Dimethyl 2,2-dimethylpentanedioate

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 2,2-dimethylpentanedioate from Step A (25.4 g, 135 mol) in MeOH (150 mL), THF (100 mL) and water (100 mL), was added potassium carbonate (36.2 g, 262 mmol). This biphasic solution was allowed to stir for 68 h, at ambient temperature, after which time the reaction was about 50% complete. Solvents were carefully removed in vacuo such that the starting materials did not vaporize. The aqueous layer was diluted with water (266 mL) and then extracted exhaustively with diethyl ether. The aqueous layer was made acidic by the addition of 6 M HCl (95 mL), saturated with NaCl, and extracted with diethyl ether (250 mL). This ethereal layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound. MS: m/z=175 (M+1).

Workup

  1. customSolvents were carefully removed in vacuo such that the starting materials
  2. additionThe aqueous layer was diluted with water (266 mL)
  3. extractionextracted exhaustively with diethyl ether
  4. additionThe aqueous layer was made acidic by the addition of 6 M HCl (95 mL), saturated with NaCl
  5. extractionextracted with diethyl ether (250 mL)
  6. washThis ethereal layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23329810dc39440bb9116249a30ba704
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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