Ethylene Glycol → HCID 178421610, compound

HRID 465508Notes

Reaction equation

HRID 465508 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[S:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:14](O)[CH2:15][OH:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1C=CC=CC=1.O.CCOCC.C(O)C>[CH3:2][C:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[S:12])=[CH:6][CH:5]=2)[O:16][CH2:15][CH2:14][O:3]1

Participants

10

Reactant 5

HCID 174Ethylene GlycolHCID 311Citric AcidHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 178466549HCID 178466549, compound

Product 1

HCID 178421610HCID 178421610, compoundYield 54.6%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-acetylphenylthioacetic acid (8.4 g, 40 mmol) (obtained as described by Walker and Leib in J. Org. Chem. 1963, 28, 3077-3082), ethylene glycol (4.96 g, 80 mmol) and a catalytic quantity of p-toluenesulphonic acid in benzene (80 ml) was heated at reflux for 16 hours using a Dean and Stark apparatus. Water (1.5 ml, 80 mmol) was collected. The solvent was removed by evaporation to give an oil. Ethanol (30 ml) and 2N sodium hydroxide solution (1 equivalent) were added and the mixture was stirred for one hour. The mixture was concentrated in vacuo. The residue was diluted with water to give a volume of 80 ml. Ether (50 ml) was added and the mixture was stirred vigorously with cooling in ice. A 10% aqueous solution of citric acid was added to give a pH of 6.5. The mixture was extracted with ether (20×50 ml). The combined extracts were dried (N2SO4) and the solvent was removed by evaporation to give a white solid. Water was added to the solid and the mixture was stirred. The solid was collected by filtration and dried in vacuo over phosphorus pentoxide. There was thus obtained 4-(2-methyl-1,3-dioxolan-2-yl)phenylthioacetic acid (B) as a solid (5.2 g, 51% yield); NMR spectrum (200 MHz, d6 -DMSO): 1.49(s, 3H), 3.62(m, 2H), 3.72(s, 2H), 3.9(m, 2H), 7.25(m,4H).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent was removed by evaporation
  3. customto give an oil
  4. concentrationThe mixture was concentrated in vacuo
  5. additionThe residue was diluted with water
  6. customto give a volume of 80 ml
  7. stirringthe mixture was stirred vigorously
  8. temperaturewith cooling in ice
  9. customto give a pH of 6.5
  10. extractionThe mixture was extracted with ether (20×50 ml)
  11. customThe combined extracts were dried (N2SO4)
  12. customthe solvent was removed by evaporation
  13. customto give a white solid
  14. stirringthe mixture was stirred
  15. filtrationThe solid was collected by filtration
  16. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-cc99fc93c44d4c97a425ccea6d56059e
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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