Phenol → 3-Phenoxy-cyclohex-2-enone

HRID 724372Notes

Reaction equation

HRID 724372 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-9e254df8eca048a397b45b9e112ddb37
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

Loading…