Water → 5-Oxo-1,3-oxathiolane-2-carboxylic acid

HRID 1939620Notes

Reaction equation

HRID 1939620 reaction equation
C1(C)C=CC=CC=1.[SH:8][CH2:9][C:10]([OH:12])=[O:11].O.[C:14]([OH:18])(=[O:17])[CH:15]=O.O>C1COCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:18]1[C:14](=[O:17])[CH2:15][S:8][CH:9]1[C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 1133Thioglycolic AcidHCID 1140TolueneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 151682115-Oxo-1,3-oxathiolane-2-carboxylic acidYield 74.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Toluene (700 mL), mercaptoacetic acid (38 mL, 50.03 g, 0.543 mol), and p-toluenesulfonic acid (1.0 g) were added to a solution of glyoxylic acid monohydrate (50.0 g, 0.543 mol) in 200 mL of THF in a 2 L round bottom flask equipped with a Dean-Stark trap and condenser. The resultant reaction mixture was refluxed for 3 hours until 24.0 mL of H2O was azeotropically removed. The reaction mixture was cooled, followed by removal of solvent under reduced pressure to yield an off-white solid. This material was purified by recrystallization (hexanes-EtOAc) to give 60.0 g of the product as a crystalline white solid: m.p. 140°-143° C.; 1H NMR (DMSO) δ 3.84 (q, 2H, JAB=16.7 Hz), 6.00 (s, 1H).

Workup

  1. customequipped with a Dean-Stark trap and condenser
  2. customThe resultant reaction mixture
  3. customwas azeotropically removed
  4. temperatureThe reaction mixture was cooled
  5. customfollowed by removal of solvent under reduced pressure
  6. customto yield an off-white solid
  7. customThis material was purified by recrystallization (hexanes-EtOAc)

Sources & evidence

ORD record
ord-a812288c20d7422d9df70309491a273e
Source dataset
uspto-grants-1997_12
Patent number
US05696254

Reaction notes

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