Water → 2-Phenoxycyclohexanone

HRID 1839174Notes

Reaction equation

HRID 1839174 reaction equation
[O:1]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O.C(OCC)C>CC(C)=O>[O:1]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 11206316Cyclohexanol, 2-phenoxy-HCID 131709961Jones' reagent

Product 1

HCID 2620892-Phenoxycyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Phenoxy-cyclohexanol (13.64 g, 0.071 mol) was dissolved in acetone (260 mL), cooled to between 0° C. to 5° C., and Jones Reagent (2 M, 78 mL) was added dropwise. The reaction was stirred for 4.5 hours. The reaction mixture was poured into water (250 mL), and diethyl ether (500 mL) was added. The organic phase was separated from the aqueous phase, then washed with water, dried (over MgSO4), and concentrated to yellow crystals. The crystals were recrystallized from pentane to give 2-phenoxy-cyclohexanone (a compound of general Formula III) (10.22 g, 76%). 1 HNMR (CDCl3): δ7.2 (m, 2H), 7.0 (m, 2H), 6.8 (d, 1H), 4.6 (m, 1H), 2.6 (m, 1H), 2.4 (m, 2H), 2.0-1.8 (m, 5H) ppm.

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. customThe organic phase was separated from the aqueous phase
  4. washwashed with water
  5. dry with materialdried (over MgSO4)
  6. concentrationconcentrated to yellow crystals
  7. customThe crystals were recrystallized from pentane

Sources & evidence

ORD record
ord-bbe9f6de000e45b8a7aba189e552af43
Source dataset
uspto-grants-2004_01
Patent number
US06677355B1

Reaction notes

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