Cyclohexene oxide → Cyclohexanol, 2-phenoxy-

HRID 1839173Notes

Reaction equation

HRID 1839173 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.O.O.O.[O-:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na+]>>[O:11]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]1[OH:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 9246Cyclohexene oxideHCID 23681143Sodium Phenoxide Trihydrate

Product 1

HCID 11206316Cyclohexanol, 2-phenoxy-

Procedure

Cyclohexene oxide (10 g, 0.102 mol) was added dropwise to an aqueous solution of sodium phenoxide trihydrate (31.6 g, 0.186 mol; 250 mL). The mixture was refluxed overnight, cooled to room temperature, and a precipitate was collected by filtration. The precipitate was dissolved in ethyl acetate. The organic phase was washed with 1 M NaOH, brine, dried (over MgSO4), and concentrated to give solid 2-phenoxy-cyclohexanol (a compound of general Formula II) (13.84 g, 70%). The melting point of this compound was determined to be 79-80° C. 1HNMR (CDCl3 ): δ7.3 (m, 2H), 6.9 (m, 3H), 4.0 (m, 1H), 3.7 (m, 1H), 2.1 (m, 2H), 1.8 (m, 4H), 1.4 (m, 4H) ppm.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationa precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in ethyl acetate
  4. washThe organic phase was washed with 1 M NaOH, brine
  5. dry with materialdried (over MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0eefde4924a74a79a7597c9c5abdbf75
Source dataset
uspto-grants-2004_01
Patent number
US06677355B1

Reaction notes

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