p-Toluenesulfonic acid monohydrate → 2-(4-Carbethoxybutyl)cyclopentan-1-one

HRID 1112635Notes

Reaction equation

HRID 1112635 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])([OH:3])=[O:2].O.[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][CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])([O:3][CH2:15][CH3:16])=[O:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 135134014-Carboxybutylcyclopentan-1-one

Product 1

HCID 130462922-(4-Carbethoxybutyl)cyclopentan-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 124 g. (0.673 mole) of 2-(4-carboxybutyl)cyclopentan-1-one (Example 2), 800 ml. of ethanol and 1 g. of p-toluenesulfonic acid monohydrate is heated at reflux for 18 hours. The solvent is evaporated and the residue is dissolved in ether. The ether solution is washed with saline, dilute sodium bicarbonate solution and again with saline, dried over magnesium sulfate and evaporated. The oil is distilled under reduced pressure to give 149 g. of a colorless oil, b.p. 106° - 109° C. (0.23 mm).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent is evaporated
  3. dissolutionthe residue is dissolved in ether
  4. washThe ether solution is washed with saline, dilute sodium bicarbonate solution and again with saline
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. distillationThe oil is distilled under reduced pressure
  8. customto give 149 g

Sources & evidence

ORD record
ord-3b9ffaf477b04607a628b6de1d614f18
Source dataset
uspto-grants-1978_10
Patent number
US04123456

Reaction notes

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