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

HRID 1701591Notes

Reaction equation

HRID 1701591 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, n.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, n.p
  10. custom147°-150° C. (0.07 Torr)

Sources & evidence

ORD record
ord-b226376a5a9d406e803bc9f1590c473f
Source dataset
uspto-grants-1980_03
Patent number
US04194055

Reaction notes

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