Ethanol → Cyclopentanecarboxylic acid, 2-hexyl-3-oxo-, ethyl ester
Reaction equation
O.[CH2:2]([CH:8]1[C:12](=[O:13])[CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:17](O)[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:2]([CH:8]1[C:12](=[O:13])[CH2:11][CH2:10][CH:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Participants
6
Procedure
In a 1 L flask, to which is attached a water separator under a reflux condenser, is placed a solution of 20 g of 2-n-hexyl-3-oxo-cyclopentanecarboxylic acid, 9,5 g of absolute ethanol and 1 g of p-toluenesulphonic acid in 500 ml of benzene. The reaction mixture is refluxed until no more water separates. The reaction mixture is then cooled and washed successively with water and sodium carbonate solution and dried over anhydrous sodium sulphate. The solvent is removed by distillation at atmospheric pressure and the residue is distilled through a short Vigreux column. Ethyl 2-n-hexyl-3-oxo-cyclopentanecarboxylate is collected at 102°C/0.25 mm, yield 19,5 g (86%), nD20 1.4535.
Workup
- customIn a 1 L flask, to which is attached
- temperatureThe reaction mixture is then cooled
- washwashed successively with water and sodium carbonate solution
- dry with materialdried over anhydrous sodium sulphate
- customThe solvent is removed by distillation at atmospheric pressure
- distillationthe residue is distilled through a short Vigreux column
- customEthyl 2-n-hexyl-3-oxo-cyclopentanecarboxylate is collected at 102°C/0.25 mm, yield 19,5 g (86%)
Sources & evidence
- ORD record
- ord-d88df1e5c8154e1abf59b906ef557bf3
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03954834
Reaction notes
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