Sodium Hydroxide → (5,6-Dihydro-1,4-oxathiin-3-yl)acetic acid

HRID 435965Notes

Reaction equation

HRID 435965 reaction equation
[OH-].[Na+].[O:3]1[CH2:8][CH2:7][S:6][C:5]([CH2:9][C:10]([O:12]CC)=[O:11])=[CH:4]1>O.C(O)C>[O:3]1[CH2:8][CH2:7][S:6][C:5]([CH2:9][C:10]([OH:12])=[O:11])=[CH:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53759655Ethyl (5,6-dihydro-1,4-oxathiin-3-yl)acetate

Product 1

HCID 54390454(5,6-Dihydro-1,4-oxathiin-3-yl)acetic acidYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of sodium hydroxide (3.2 g.) in water (18 cc.) is added to a solution of ethyl (5,6-dihydro-1,4-oxathiin-3-yl )acetate (13.4 g.) in ethanol (134 cc.). The reaction mixture is heated for one hour at 60° C. and is then concentrated to dryness under reduced pressure (20 mm.Hg). The resulting residue is taken up in water (250 cc.), and the mixture extracted with diethyl ether (200 cc.), decanted and the ether phase is discarded. The aqueous phase is acidified to pH 1 by addition of 4N hydrochloric acid and is then extracted three times with diethyl ether (total 600 cc.). The ether fractions are combined, washed twice with water (total 200 cc.), dried over sodium sulphate and treated with decolourizing charcoal. After filtration and concentration to dryness under reduced pressure (20 mm.Hg), (5,6-dihydro-1,4-oxathiin-3-yl )acetic acid (8.9 g.) is obtained in the form of an oil which is used as it is.

Workup

  1. concentrationis then concentrated to dryness under reduced pressure (20 mm.Hg)
  2. extractionthe mixture extracted with diethyl ether (200 cc.)
  3. customdecanted
  4. additionThe aqueous phase is acidified to pH 1 by addition of 4N hydrochloric acid
  5. extractionis then extracted three times with diethyl ether (total 600 cc.)
  6. washwashed twice with water (total 200 cc.)
  7. dry with materialdried over sodium sulphate
  8. additiontreated with decolourizing charcoal
  9. filtrationAfter filtration and concentration to dryness under reduced pressure (20 mm.Hg)

Sources & evidence

ORD record
ord-05ed6a8868024645b3c019be89b39f24
Source dataset
uspto-grants-1977_02
Patent number
US04007176

Reaction notes

Loading…