Acetic Acid → 4-Carboxybutylcyclopentan-1-one

HRID 435782Notes

Reaction equation

HRID 435782 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15])([O:3]CC)=[O:2].Cl.C(O)(=O)C>O>[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 130462922-(4-Carbethoxybutyl)cyclopentan-1-one

Product 1

HCID 135134014-Carboxybutylcyclopentan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 274 g. of 2-carbalkoxy(mixed methyl and ethyl esters)-2-(4-carbethoxybutyl)cyclopentan-1-one (Example 1), 600 ml. of 20% hydrochloric acid and 325 ml. of acetic acid is heated at reflux for 20 hours. Solution occurs in approximately 1/2 hour. The solution is cooled and diluted with water and extracted with ether. The combined extracts are washed with saline and dried over magnesium sulfate and evaporated. The residue is evaporated twice with toluene to give 144 g. of an oil.

Workup

  1. additionA stirred mixture of 274 g
  2. temperatureat reflux for 20 hours
  3. temperatureThe solution is cooled
  4. extractionextracted with ether
  5. washThe combined extracts are washed with saline
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue is evaporated twice with toluene
  9. customto give 144 g

Sources & evidence

ORD record
ord-6bd3ee2225b14b8e9fbefd0780936d67
Source dataset
uspto-grants-1977_02
Patent number
US04006179

Reaction notes

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