Lithium hydroxide, monohydrate → trans-2-(4-Bromophenoxy)cyclohexanol

HRID 2360337Notes

Reaction equation

HRID 2360337 reaction equation
C([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)(=O)C.O.[OH-].[Li+]>CO.O>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C@@H:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]2[OH:4])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67197945(1R,2R)-2-(4-bromophenoxy)cyclohexyl acetate

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (1R,2R)-2-(4-bromophenoxy)cyclohexyl acetate (2.047 g, 6.54 mmol) in methanol (12.2 mL) and water (0.32 mL) was cooled to 0° C. and treated with lithium hydroxide hydrate (95%, 1.73 g, 39.2 mmol). The reaction was stirred at 0° C. for 15 minutes, then allowed to warm and stir at room temperature for 18 hours. The methanol was removed under reduced pressure, and the aqueous residue was partitioned between ethyl acetate (200 mL) and water (100 mL). After extraction of the aqueous layer with ethyl acetate (100 mL), the combined organics were washed with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to provide (1R,2R)-2-(4-bromophenoxy)cyclohexanol as a yellow oil. Yield: 1.76 g, 6.49 mmol, 99%. 1H NMR (400 MHz, CDCl3) δ 1.26-1.46 (m, 4H), 1.74-1.79 (m, 2H), 2.08-2.14 (m, 2H), 3.72 (ddd, J=10.5, 8.4, 4.7 Hz, 1H), 3.96 (m, 1H), 6.84 (d, J=9.0 Hz, 2H), 7.37 (d, J=9.0 Hz, 2H).

Workup

  1. temperatureto warm
  2. stirringstir at room temperature for 18 hours
  3. customThe methanol was removed under reduced pressure
  4. customthe aqueous residue was partitioned between ethyl acetate (200 mL) and water (100 mL)
  5. extractionAfter extraction of the aqueous layer with ethyl acetate (100 mL)
  6. washthe combined organics were washed with saturated aqueous sodium chloride solution (100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-643fb9f1c8844de487735368a23ecee2
Source dataset
uspto-grants-2014_04
Patent number
US08686043B2

Reaction notes

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