Sodium Hydroxide → 5,5-Dimethoxypentanoic acid

HRID 2393687Notes

Reaction equation

HRID 2393687 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO>[CH3:12][O:11][CH:3]([O:2][CH3:1])[CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 551444Methyl 5,5-dimethoxyvalerate

Product 1

HCID 118050725,5-Dimethoxypentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

12 mmoles methyl 5,5-dimethoxypentanoate (Stevens, R. V. et al., J Am Chem Soc (1979) 7054) were dissolved in 20 ml 50% aqueous methanol. 16 mmoles NaOH were added and the mixture was stirred for 2 hr at room temperature. The solvent was then evaporated, the residue layered with 30 ml EtOAc, and the sodium salt neutralized with ice-cold 1N HCl. The aqueous phase was extracted with an additional 20 ml EtOAc, the organic extracts combined and dried over K2CO3. The product was filtered and the solvent evaporated to provide 5,5-dimethoxypentanoic acid.

Workup

  1. customThe solvent was then evaporated
  2. extractionThe aqueous phase was extracted with an additional 20 ml EtOAc
  3. dry with materialdried over K2CO3
  4. filtrationThe product was filtered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-f0f9e1b9ecc04f6c96d765e11669395d
Source dataset
uspto-grants-1998_09
Patent number
US05807979

Reaction notes

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