Methanol → Tetrahydropyran-4-ylacetic acid

HRID 1755673Notes

Reaction equation

HRID 1755673 reaction equation
CO.[OH-].[Na+].[O:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]([O:14]CC)=[O:13])[CH2:7][CH2:6]1>O>[O:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]([OH:14])=[O:13])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2773412Ethyl tetrahydropyran-4-ylacetate

Product 1

HCID 2773575Tetrahydropyran-4-ylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

20 ml of methanol, 10 ml of water and 1 g of sodium hydroxide were added to 0.9 g of ethyl 4-tetrahydropyranylacetate and agitated at 80° C. for 1 hour. The solvent was removed by distillation, to which water was added. After washing with ethyl acetate, a hydrochloric acid aqueous solution was added to the resultant aqueous phase to an extract of pH of 3, followed by extraction with chloroform under salting-out conditions and drying with anhydrous magnesium sulfate. This was removed by filtration and the solvent was distilled off, thereby obtaining 0.87 g of a crude intended compound.

Workup

  1. customThe solvent was removed by distillation, to which water
  2. additionwas added
  3. washAfter washing with ethyl acetate
  4. additiona hydrochloric acid aqueous solution was added to the resultant aqueous phase to
  5. extractionan extract of pH of 3
  6. extractionfollowed by extraction with chloroform under salting-out conditions
  7. dry with materialdrying with anhydrous magnesium sulfate
  8. customThis was removed by filtration
  9. distillationthe solvent was distilled off
  10. customobtaining 0.87 g of a crude intended compound

Sources & evidence

ORD record
ord-ce17988df67f43208ad13950e8cb9e22
Source dataset
uspto-grants-1995_08
Patent number
US05438045

Reaction notes

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