Cyclohexanone → Cyclohexanone, 2-(2-ethoxyethyl)-
Reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OOC(C)(C)C)(C)(C)C.[CH:18]([O:20][CH2:21][CH3:22])=[CH2:19]>>[CH2:18]([O:20][CH2:21][CH2:22][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:1]1=[O:7])[CH3:19]Participants
Procedure
2940 g (30 mol) of cyclohexanone were heated to reflux while stirring and, at this temperature, a solution of 87.6 g (0.6 mol) of di-tert-butyl peroxide in 216 g (3 mol) of ethyl vinyl ether was added over the course of 5 hours (h). The mixture was subsequently refluxed for a further 1 h. After the mixture had cooled, the low boilers (tert-butanol, remaining vinyl ether and peroxide) and the excess cyclohexanone were removed by distillation under reduced pressure (25-40 mbar; diaphragm pump). The residue (about 500 g) was distilled under reduced pressure (0.5 to 2 mbar; oil pump). A total of 350 g of a 95% pure 2-(2-ethoxyethyl)cyclohexanone of boiling point 60°-65° C. (0.5 mbar) was obtained, corresponding to a yield of 69% of theory.
Workup
- temperatureto reflux
- temperatureThe mixture was subsequently refluxed for a further 1 h
- temperatureAfter the mixture had cooled
- customthe low boilers (tert-butanol, remaining vinyl ether and peroxide) and the excess cyclohexanone were removed by distillation under reduced pressure (25-40 mbar; diaphragm pump)
- distillationThe residue (about 500 g) was distilled under reduced pressure (0.5 to 2 mbar; oil pump)
Sources & evidence
- ORD record
- ord-dd98fc9de58c4f739bd0b7fa2a95a3bf
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380920
Reaction notes
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