Sodium borohydride → 4-(4-Bromophenoxy)cyclohexanol

HRID 1183934Notes

Reaction equation

HRID 1183934 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 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. customquenched by the addition of 1 N HCl (aq)
  2. concentrationThe reaction was concentrated
  3. customthe resulting residue was partitioned between ether and 1 N 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 SF15-12 g column (hexanes/ethyl acetate=8:2)

Sources & evidence

ORD record
ord-61c59a4b5d5b4c558a056160d1c019b6
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Reaction notes

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