Potassium Hydroxide → (2R,3R)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid

HRID 414858Notes

Reaction equation

HRID 414858 reaction equation
[O:1]1[C@@H:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@@H:2]1[C:3]([O:5]CC)=[O:4].[OH-].[K+]>C(O)C>[CH2:12]([O:11][C:9](=[O:10])[C@@H:8]1[O:1][C@H:2]1[C:3]([OH:5])=[O:4])[CH3:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 27336462,3-diethyl (2R,3R)-oxirane-2,3-dicarboxylate

Product 1

HCID 13150798(2R,3R)-3-(ethoxycarbonyl)oxirane-2-carboxylic acidYield 42.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 50 ml of ethanol is dissolved 13.1 g (69.7 mmole), of diethyl (2R,3R)-epoxysuccinate, and a solution of 3.94 g of potassium hydroxide in 120 ml of ethanol is added dropwise to the solution under ice-cooling with stirring. After the stirring under ice-cooling for 3 hours, the ethanol is distilled off under reduced pressure. 50 ml of water and 100 ml of ether are added to the residue to a solution, and the aqueous layer is separated. The ether layer is extracted three times with dilute aqueous sodium chloride solution, and the aqueous layers are combined and acidified with 3N hydrochloric acid. The solution, after being saturated with sodium chloride, is extracted four times with ethyl acetate, and the extract is washed with aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is distilled under reduced pressure to give 4.76 g (42.7%) of (2R,3R)-epoxysuccinic acid monoethyl ester as a colorless oil having a boiling point of 121°-122° C. (0.85 mmHg). The product, upon standing, crystallizes, and the crystals are recrystallized from isopropyl ether-petroleum ether (1:2) to give colorless crystals.

Workup

  1. temperaturecooling
  2. temperatureAfter the stirring under ice-cooling for 3 hours
  3. distillationthe ethanol is distilled off under reduced pressure
  4. addition50 ml of water and 100 ml of ether are added to the residue to a solution
  5. customthe aqueous layer is separated
  6. extractionThe ether layer is extracted three times with dilute aqueous sodium chloride solution
  7. extractionis extracted four times with ethyl acetate
  8. washthe extract is washed with aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent is distilled off under reduced pressure
  11. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-4e491d9de83e4edb80732b99e257c1b2
Source dataset
uspto-grants-1988_12
Patent number
US04794108

Reaction notes

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