Acetic Acid → 4-Carboxybutylcyclopentan-1-one

HRID 973003Notes

Reaction equation

HRID 973003 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 one-half 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. waitSolution occurs in approximately one-half hour
  4. temperatureThe solution is cooled
  5. extractionextracted with ether
  6. washThe combined extracts are washed with saline
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue is evaporated twice with toluene
  10. customto give 144 g

Sources & evidence

ORD record
ord-f99be0c5f4154c918269bbd3f01e1edc
Source dataset
uspto-grants-1977_10
Patent number
US04054604

Reaction notes

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