Sodium borohydride → 4-(4-Bromophenoxy)cyclohexanol

HRID 709208Notes

Reaction equation

HRID 709208 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

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 00° C. and quenched by the addition of 1 N HCl (aq). The reaction was concentrated and the resulting residue was partitioned between ether and 1 N HCl (aq). The layers were separated, the organic layer was washed with water then dried (Na2SO4), filtered and concentrated. Purification on an Analogix SF15-12 g column (hexanes/ethyl acetate=8:2) afforded the title compound as a white solid (360 mg, 72%).

Workup

  1. temperatureAfter 20 minutes the reaction was cooled to 00° C
  2. customand quenched by the addition of 1 N HCl (aq)
  3. concentrationThe reaction was concentrated
  4. customthe resulting residue was partitioned between ether and 1 N HCl (aq)
  5. customThe layers were separated
  6. washthe organic layer was washed with water
  7. dry with materialthen dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification on an Analogix SF15-12 g column (hexanes/ethyl acetate=8:2)

Sources & evidence

ORD record
ord-c04ad4b26c8240ef8feb0cef81da6354
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

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