Cyclohexanone → HCID 12943602, compound

HRID 849148Notes

Reaction equation

HRID 849148 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][CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1.S([O-])(O)(=O)=O.[K+].CCOCC.O>[CH2:19]([O:18][CH2:17][CH2:16][CH2:15][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:7]1=[O:13])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 3

HCID 7967CyclohexanoneHCID 2776064Benzyl 3-Bromopropyl EtherHCID 23665647Potassium tert-butoxide

Product 1

HCID 12943602HCID 12943602, compoundYield 93.9%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 516920Potassium bisulfateSolvent2×

Conditions

Temperature
0 °C

Procedure

Example 234 A) To a mechanically stirred mixture of KOt-Bu (10.1 g, 104 mmol) in benzene (100 mL) cooled to 0° C. under nitrogen was added cyclohexanone (7.4 g, 83 mmol) dropwise over 20 min. Ten minutes after the addition was complete, benzyl 3-bromo-propyl ether (20 g, 87 mmol) was added over a twenty minute period. The reaction mixture was warmed to room temperature, refluxed for seven hours, stirred at room temperature or eighteen hours, and diluted with 0.5N potassium hydrogen sulfate (200 mL). The reaction mixture was further diluted with Et2O, 0.5N potassium hydrogen sulfate, and water, until two phases formed. The organic phase was washed with water, brine, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure to give 19.2 g of the 2-(3-benzyloxypropyl)-cyclohexan-1-one.

Workup

  1. additionTen minutes after the addition
  2. temperatureThe reaction mixture was warmed to room temperature
  3. temperaturerefluxed for seven hours
  4. customformed
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6bf63e34c7a74080b69b2b111ecf0f4f
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

Loading…