Acetic Acid → 4-Carboxybutylcyclopentan-1-one

HRID 1903925Notes

Reaction equation

HRID 1903925 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. temperatureat reflux for 20 hours
  2. temperatureThe solution is cooled
  3. extractionextracted with ether
  4. washThe combined extracts are washed with saline
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue is evaporated twice with toluene
  8. customto give 144 g

Sources & evidence

ORD record
ord-54c6a192556e44dea9a0e3ba97dac591
Source dataset
uspto-grants-1984_03
Patent number
US04439365

Reaction notes

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