Water → ((4-Cyclohexylphenoxy)methyl)oxirane

HRID 221948

Reaction equation

HRID 221948 reaction equation
[CH2:1]1[O:3][C@H:2]1[CH2:4]Cl.[CH:6]1([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C>[CH:6]1([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:4][CH:2]3[CH2:1][O:3]3)=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 143274-CyclohexylphenolHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 5743581((4-Cyclohexylphenoxy)methyl)oxirane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of R-epichlorohydrin (9.8 g, 106 mmol) and 4-cyclohexylphenol (3.73 g, 21.2 mmol) in acetonitrile (40 ml) was added cesium carbonate (6.9 g, 21.2 mmol). The mixture was heated at reflux for 3 hours. The reaction mixture was cooled, poured into water (100 mL) and extracted twice with EtOAc. The organic phases were combined and washed with water, brine, dried (Na2SO4), concentrated and dried under high vacuum overnight to give the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted twice with EtOAc
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-d3037173a1b8480bbbcf4512227dd842
Source dataset
uspto-grants-2012_06
Patent number
US08207181B2

Linked notes

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