Cyclohexanone Oxime → 3-[(Cyclohexylideneamino)oxy]propanoic acid
Reaction equation
[C:1]1(=[N:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([O:13]CC)(=[O:12])[CH:10]=[CH2:11].[OH-].[K+]>C(O)C>[C:1]1(=[N:7][O:8][CH2:11][CH2:10][C:9]([OH:13])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 32.8 g (0.29 mol) of cyclohexanone oxime, 26 g (0.26 mmol) of ethyl acrylate, 26 ml (0.052 mol) of a 2N solution of KOH in ethanol and 150 ml of ethanol is stirred for 96 hours at 60° C. and afterwards concentrated on a vacuum rotary evaporator. The residue (an orange oil) is dissolved in 175 g (0.31 tool) of a 10% solution of KOH in ethanol and the solution is heated for 1 hour to 60° C. The solvent is distilled off and the solid residue is taken up in water. After acidification with c. 15 ml of conc. hydrochloric acid and extraction with ethyl acetate, the organic phase is washed with water, dried over Na2SO4 and concentrated on a vacuum rotary evaporator. Distillation of the residue yields 11.8 g (25%) of the desired acid as an orange liquid. The boiling point is 135° C./0.05 mbar.
Workup
- concentrationafterwards concentrated on a vacuum rotary evaporator
- dissolutionThe residue (an orange oil) is dissolved in 175 g (0.31 tool) of a 10% solution of KOH in ethanol
- temperaturethe solution is heated for 1 hour to 60° C
- distillationThe solvent is distilled off
- extraction15 ml of conc. hydrochloric acid and extraction with ethyl acetate
- washthe organic phase is washed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated on a vacuum rotary evaporator
- distillationDistillation of the residue
Sources & evidence
- ORD record
- ord-2f76d6ee00514261b05b6fa40148cab8
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05602196
Reaction notes
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