p-Toluenesulfonic acid → Ethyl {[5-(5-oxocyclopent-1-en-1-yl)pentyl]sulfanyl}acetate

HRID 1447944Notes

Reaction equation

HRID 1447944 reaction equation
[C:1]([CH2:4][S:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:12](=[O:16])[CH2:13][CH2:14][CH:15]=1)([OH:3])=[O:2].[C:17]1(C)C=CC(S(O)(=O)=O)=C[CH:18]=1>C(O)C>[C:1]([CH2:4][S:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:12](=[O:16])[CH2:13][CH2:14][CH:15]=1)([O:3][CH2:17][CH3:18])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20347252{[5-(5-Oxocyclopent-1-en-1-yl)pentyl]sulfanyl}acetic acid

Product 1

HCID 20347243Ethyl {[5-(5-oxocyclopent-1-en-1-yl)pentyl]sulfanyl}acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 74 g. (0.306 mols) of 2-(7-carboxy-6-thiaheptyl)-2-cyclopentenone, 1200 ml. of ethanol and 1 g. p-toluenesulfonic acid is stirred and refluxed for 18 hours. The resulting solution is concentrated and the residue is dissolved in ether. The organic phase is washed with water, sodium bicarbonate solution and saline, dried (MgSO4) and evaporated. The residue is distilled to give a light yellow oil, o.p. 147°-150° C. (0.07 Torr).

Workup

  1. additionA mixture of 74 g
  2. temperaturerefluxed for 18 hours
  3. concentrationThe resulting solution is concentrated
  4. dissolutionthe residue is dissolved in ether
  5. washThe organic phase is washed with water, sodium bicarbonate solution and saline
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. distillationThe residue is distilled
  9. customto give a light yellow oil, o.p
  10. custom147°-150° C. (0.07 Torr)

Sources & evidence

ORD record
ord-844498fe1b6e403285e0153c0ecfeeab
Source dataset
uspto-grants-1979_12
Patent number
US04178461

Reaction notes

Loading…