Phenol → 3-Phenoxy-cyclohex-2-enone

HRID 1862107Notes

Reaction equation

HRID 1862107 reaction equation
Cl[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[O:8]([C:11]1[CH2:12][CH2:13][CH2:14][C:9](=[O:15])[CH:10]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 5683453-Chlorocyclohex-2-en-1-one

Product 1

HCID 36542163-Phenoxy-cyclohex-2-enone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-chloro-cyclohex-2-enone (3.00g, 23.0 mmol) and phenol (2.16 g, 23.0 mmol) in 25 mL of acetone was added powdered, anhydrous K2CO3 (3.81 g, 27.6 mmol). After refluxing for 18 h, the mixture was cooled and filtered. The filtrate was concentrated under reduced pressure and chromatographed on silica gel eluting with hexanes/EtOAc (4:1) to give 3-phenoxy-cyclohex-2-enone as a white solid: 1H NMR (CDCl3) δ 2.10 (quint, 2H, J=6.3 Hz), 2.40 (t, 2H, J=6.2 Hz), 2.68 (t, 2H, J=6.3 Hz), 5.14 (s, 1H), 7.05 (d, 2H, J=7.5 Hz), 7.26 (t, 1H, J=7.3 Hz), 7.41 (t, 2H, J=7.6 Hz).

Workup

  1. temperatureAfter refluxing for 18 h
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customchromatographed on silica gel eluting with hexanes/EtOAc (4:1)

Sources & evidence

ORD record
ord-f4a94f8e1b5a43a29fb6773d9552d347
Source dataset
uspto-grants-2003_03
Patent number
US06534524B1

Reaction notes

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