Sodium borohydride → 4-(4-Bromophenoxy)cyclohexanol

HRID 1475818Notes

Reaction equation

HRID 1475818 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1>C(O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]2[CH2:10][CH2:11][CH:12]([OH:15])[CH2:13][CH2:14]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 672488834-(4-Bromophenoxy)cyclohexanone

Product 1

HCID 672496744-(4-Bromophenoxy)cyclohexanolYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (77.3 mg, 2.04 mmol) was added to a solution of 4-(4-bromophenoxy)cyclohexanone (500 mg, 1.86 mmol) in ethanol (10 mL) at room temperature. After 20 minutes the reaction was cooled to 0° C. and quenched by the addition of 1N HCl (aq). The reaction was concentrated and the resulting residue was partitioned between ether and 1N HCl (aq). The layers were separated, the organic layer was washed with water then dried (Na2SO4), filtered and concentrated. Purification on an Analogix SF15-12g column (hexanes/ethyl acetate=8:2) afforded the title compound as a white solid (360 mg, 72%).

Workup

  1. customquenched by the addition of 1N HCl (aq)
  2. concentrationThe reaction was concentrated
  3. customthe resulting residue was partitioned between ether and 1N HCl (aq)
  4. customThe layers were separated
  5. washthe organic layer was washed with water
  6. dry with materialthen dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification on an Analogix SF15-12g column (hexanes/ethyl acetate=8:2)

Sources & evidence

ORD record
ord-1e63593ca7ed4c23a289b17dcb26f940
Source dataset
uspto-grants-2015_04
Patent number
US09018384B2

Reaction notes

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