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

HRID 1605766Notes

Reaction equation

HRID 1605766 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 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-e0c5d4b88d6e486ba83dc62f04777b85
Source dataset
uspto-grants-1976_04
Patent number
US03950406

Reaction notes

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