Ethylene Glycol → HCID 57234343, compound

HRID 1032635Notes

Reaction equation

HRID 1032635 reaction equation
[O:1]=[C:2]([CH3:14])[CH:3](SC(=O)C)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:15](O)[CH2:16][OH:17].C1(C)C=[CH:23][C:22]([S:25](O)(=O)=O)=CC=1.[OH2:30]>C1C=CC=CC=1>[CH3:14][C:2]1([CH:3]([O:30][C:22](=[S:25])[CH3:23])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:1][CH2:15][CH2:16][O:17]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 14855973S-(2-Oxo-1-phenylpropyl) ethanethioate

Product 1

HCID 57234343HCID 57234343, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 9.4 g (0.045 mol) of ethanethioic acid S-(2-oxo-1-phenylpropyl)ester and 3.1 g (0.05 mol) of ethylene glycol in 125 ml of benzene was added 1.0 g p-toluenesulfonic acid. The mixture was then heated at reflux over a period of 10 hours while the water formed was removed with the aid of a Dean-Stark trap. The mixture was concentrated under reduced pressure and the residue 11.0 g was chromatographed on 150 g of silica gel. The column was eluted with methylene chloride and fractions 6-20 were collected. Removal of the solvent gave 7.6 g (67%) of rac.-ethanethioic acid-[(2-methyl-1,3-dioxolan-2-yl)phenylmethyl]ester. A sample of this compound was crystallized from pet. ether, mp 49°-52°.

Workup

  1. temperatureThe mixture was then heated
  2. customformed
  3. customwas removed with the aid of a Dean-Stark trap
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue 11.0 g was chromatographed on 150 g of silica gel
  6. washThe column was eluted with methylene chloride and fractions 6-20
  7. customwere collected
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-ab7dcedea96b49ca96b95f611ee65fb6
Source dataset
uspto-grants-1990_09
Patent number
US04959359

Reaction notes

Loading…