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

HRID 1590088Notes

Reaction equation

HRID 1590088 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>[C:9]([CH2:8][CH2:7][C:2]([CH3:13])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 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 962WaterSolvent

Procedure

The diester from Step 1 (13.0 g), K2CO3 (19.1 g), MeOH (120 mL), THF (80 mL) and H2O (80 mL) were stirred at room temperature for 2 days. The organic solvent was removed in vacuo, the residue poured onto H2O and extracted twice with EtOAc. The aqueous layer was acidified with 3N HCl and extracted with EtOAc (3×). This organic phase was then washed with brine, dried and evaporated to yield the title compound.

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionthe residue poured onto H2O
  3. extractionextracted twice with EtOAc
  4. extractionextracted with EtOAc (3×)
  5. washThis organic phase was then washed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-1a9bbf3ea3a6482e9595df176ca2ab37
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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