Sodium borohydride → 4-(4-Bromophenoxy)cyclohexanol

HRID 84226Notes

Reaction equation

HRID 84226 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)cyclohexanol

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.

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

Sources & evidence

ORD record
ord-a6315e0a6ab34993b4d5a5d52a3f94b8
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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