Cyclohexanone → 2-(2-Methoxyethyl)cyclohexanone
Reaction equation
CC([O-])(C)C.[K+].[C:7]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:15][CH2:16][O:17][CH3:18]>C1C=CC=CC=1.S([O-])(O)(=O)=O.[K+].CCOCC.O>[CH3:18][O:17][CH2:16][CH2:15][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:7]1=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 0 °C
Procedure
Example 241 A) To a mechanically stirred mixture of KOt-Bu (87 g, 0.9 mol) in benzene (700 mL) cooled to 0° C. under an N2 atmosphere was added cyclohexanone (67 g, 0.75 mol) dropwise over 15 minutes. Ten minutes after the addition was complete, bromoethyl methylether (90 g, 0.78 mol) was added dropwise over 20 minutes. The reaction mixture was warmed to room temperature, refluxed for 7 hours, stirred at room temperature for 18 hours, and diluted with 0.5N potassium hydrogen sulfate (300 mL). The mixture was further diluted with Et2O (600 mL), 0.5N potassium hydrogen sulfate (200 mL), and water (200 mL) before the organic phase was separated. The organic layer was washed with water (200 mL) and brine (200 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was distilled to afford 41 g (25% yield) of 2-(2-methoxyethyl)cyclohexanone.
Workup
- additionTen minutes after the addition
- temperatureThe reaction mixture was warmed to room temperature
- temperaturerefluxed for 7 hours
- customwas separated
- washThe organic layer was washed with water (200 mL) and brine (200 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- distillationThe crude product was distilled
Sources & evidence
- ORD record
- ord-85c8193d521d4289bff90074b549c7d0
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06011028
Reaction notes
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