Phenol → 3-Phenoxy-cyclohex-2-enone

HRID 2181509Notes

Reaction equation

HRID 2181509 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 (3.00 g, 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-e3f8afc62e2745559f427368a45f6ff7
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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