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

HRID 442078Notes

Reaction equation

HRID 442078 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-toluensulfonic 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 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-68009de9282144d8929db6509c764478
Source dataset
uspto-grants-1977_08
Patent number
US04044043

Reaction notes

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