Acetic Acid → 4-Carboxybutylcyclopentan-1-one
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
Product 1
Reagents, catalysts & solvents 1
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
- additionA stirred mixture of 274 g
- temperatureat reflux for 20 hours
- temperatureThe solution is cooled
- extractionextracted with ether
- washThe combined extracts are washed with saline
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue is evaporated twice with toluene
- 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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