Acetic Acid → 4-Carboxybutylcyclopentan-1-one

HRID 649071Notes

Reaction equation

HRID 649071 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 4), 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-cfd1478d36344c6b8ea3f8e9ce3361ec
Source dataset
uspto-grants-1988_04
Patent number
US04737590

Reaction notes

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