4-Bromophenol → trans-2-(4-Bromophenoxy)cyclohexanol

HRID 2360335Notes

Reaction equation

HRID 2360335 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH:10]12[O:16][CH:15]1[CH2:14][CH2:13][CH2:12][CH2:11]2>C(O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C@@H:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C@H:15]2[OH:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 9246Cyclohexene oxideHCID 5360545Sodium

Product 1

HCID 67195202trans-2-(4-Bromophenoxy)cyclohexanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (2.58 g, 112 mmol) was combined with absolute ethanol (200 mL) and allowed to react completely. 4-Bromophenol (19.4 g, 112 mmol) was added, and the reaction was stirred for 20 minutes, at which point 7-oxabicyclo[4.1.0]heptane (10.0 g, 102 mmol) was added, and the solution was heated at reflux for 15 hours. After removal of solvent in vacuo, the residue was partitioned between water (300 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (2×100 mL), and the combined organic layers were washed with water (2×200 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting light tan solid was recrystallized from heptane (roughly 200 mL) to provide trans-2-(4-bromophenoxy)cyclohexanol as a fluffy white solid. Yield: 12.5 g, 46.1 mmol, 45%. 1H NMR (400 MHz, CDCl3) δ 1.26-1.46 (m, 4H), 1.75-1.79 (m, 2H), 2.08-2.14 (m, 2H), 2.52 (d, J=2.1 Hz, 1H), 3.72 (m, 1H), 3.96 (ddd, J=10.3, 8.6, 4.4 Hz, 1H), 6.84 (d, J=9.0 Hz, 2H), 7.37 (d, J=9.0 Hz, 2H).

Workup

  1. customto react completely
  2. additionwas added
  3. temperaturethe solution was heated
  4. temperatureat reflux for 15 hours
  5. customAfter removal of solvent in vacuo
  6. customthe residue was partitioned between water (300 mL) and ethyl acetate (100 mL)
  7. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  8. washthe combined organic layers were washed with water (2×200 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting light tan solid was recrystallized from heptane (roughly 200 mL)

Sources & evidence

ORD record
ord-27faebb9060f4c0593c256b5f2d9cb63
Source dataset
uspto-grants-2014_04
Patent number
US08686043B2

Reaction notes

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