Acetic Acid → HCID 15827855, compound

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

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.