Acetic Acid → (R)-2-(Tetrahydropyranyloxy)propionic acid

In ethanol (510 ml) was dissolved methyl (2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionate (42.7 g), to which was added, under ice-cooling, a 2N solution of sodium hydroxide (170 ml), followed by stirring for one hour at room temperature. The reaction mixture was cooled with ice, to which was added a 26% aqueous solution of acetic acid (120 ml), followed by extraction with dichloromethane (200 ml) three times. Dichloromethane layers were combined, washed with a saturated aqueous sodium chloride solution (100 ml) twice, and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure to leave (2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionic acid (32 g) as a colorless waxy product.

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 sodium chloride solution (100 ml) twice
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationby distilling off the solvent under reduced pressure

ORD record

ord-7d18882e100a427eb117b1010d886a12

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05405861