p-Toluenesulfonic acid → Ethyl 6-(5-oxocyclopent-1-en-1-yl)hexanoate

HRID 1448209Notes

Reaction equation

HRID 1448209 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]=1)([OH:3])=[O:2].[C:15]1(C)C=CC(S(O)(=O)=O)=C[CH:16]=1>C(O)C>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]=1)([O:3][CH2:15][CH3:16])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 30402535-Oxo-1-cyclopentenehexanoic acid

Product 1

HCID 21767821Ethyl 6-(5-oxocyclopent-1-en-1-yl)hexanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.309 g. (0.00668 mole) of 2-(5-carboxypentyl)-2-cyclopentenone (Example 52) and 90 mg. of p-toluenesulfonic acid in 150 ml. of ethanol is refluxed for 18 hours. The solvent is evaporated and the residue is dissolved in ether. The organic phase is washed with water, sodium bicarbonate solution, and saturated saline solution, dried (MgSO4), and evaporated to give 1.371 g. of a light yellow oil.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in ether
  3. washThe organic phase is washed with water, sodium bicarbonate solution, and saturated saline solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give 1.371 g

Sources & evidence

ORD record
ord-4c5cf580d1314dffa09e77b76773ba95
Source dataset
uspto-grants-1979_12
Patent number
US04179574

Reaction notes

Loading…