Acetic Acid → 4-Carboxybutylcyclopentan-1-one

HRID 1732498Notes

Reaction equation

HRID 1732498 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-b527501ead6d464eaee8e49be1eb923e
Source dataset
uspto-grants-1980_12
Patent number
US04237316

Reaction notes

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