Methanol → Oxane-4-carboxylic acid

HRID 1798922Notes

Reaction equation

HRID 1798922 reaction equation
[OH-].[Na+].[O:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1.CO>C1COCC1>[O:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

Product 1

HCID 219302Oxane-4-carboxylic acidYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (7.05 mL, 12.5 M, 88 mmol) was added dropwise to a solution of methyl tetrahydro-2H-pyran-4-carboxylate (2.54 g, 17.6 mmol) in a mix of methanol (30 mL) and THF (30 mL) at 25° C. The reaction was stirred over the weekend. The THF/MeOH was then evaporated and the crude was washed with Et2O (2×). The aqueous layer was acidified and extracted with EtOAc (2×); the organics were dried over Na2SO4, filtered and the solvent was evaporated to give the title compound (D8) (1.94 g, 76%) as a white solid.

Workup

  1. customThe THF/MeOH was then evaporated
  2. washthe crude was washed with Et2O (2×)
  3. extractionextracted with EtOAc (2×)
  4. dry with materialthe organics were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b94b74c7368645ddaef750223c6ef090
Source dataset
uspto-grants-2013_01
Patent number
US08344000B2

Reaction notes

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