Acetic Acid → HCID 15827855, compound

HRID 1654187Notes

Reaction equation

HRID 1654187 reaction equation
[OH-].[Na+].C(O)(=O)C.[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][C@@H:14]([CH3:20])[C:15]([O:17]CC)=[O:16]>C(O)C>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][C@@H:14]([CH3:20])[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 10397939AG-G-89175

Product 1

HCID 15827855HCID 15827855, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (450 ml) was dissolved ethyl(2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionate, to which was added, under ice-cooling, 2N sodium hydroxide solution (150 ml), and the mixture was stirred for one hour at room temperature. The reaction mixture was cooled with ice, to which was added a 27° C. aqueous solution of acetic acid (100 ml), followed by extraction with dichloromethane (200 ml) three times. Dichloromethane layers were combined and washed with a saturated aqueous saline solution (100 ml) twice, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave (2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionic acid (29.5 g) as a colorless waxy product.

Workup

  1. additionto which was added, under ice-
  2. temperaturecooling
  3. temperatureThe reaction mixture was cooled with ice, to which
  4. extractionfollowed by extraction with dichloromethane (200 ml) three times
  5. washwashed with a saturated aqueous saline solution (100 ml) twice
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c8581ffa6e69462b89d459cd128f7ce9
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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