Sodium borohydride → 1-Bromo-trans-1-octen-3-ol

HRID 1439679Notes

Reaction equation

HRID 1439679 reaction equation
[BH4-].[Na+].[Br:3]/[CH:4]=[CH:5]/[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C(O)C>[Br:3]/[CH:4]=[CH:5]/[CH:6]([OH:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117903381-Bromo-trans-1-octen-3-one

Product 1

HCID 130462801-Bromo-trans-1-octen-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice cooled mixture of 20 g. of sodium borohydride in 800 ml. of anhydrous ethanol is added 160 g. of crude 1-bromo-trans-1-octen-3-one (Example 992) over a period of 0.5 hour. The mixture is stirred for 2 hours with ice cooling and is then partitioned between ice water and benzene. The organic phase is washed with water and saturated brine, dried (Na2SO4), and evaporated to an oil. Distillation gives the product as an oil, b.p. 66°-68° C. (0.025 torr.).

Workup

  1. additionmixture of 20 g
  2. customis then partitioned between ice water and benzene
  3. washThe organic phase is washed with water and saturated brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to an oil
  6. distillationDistillation

Sources & evidence

ORD record
ord-284e7f7da6eb4e5ca89496bc7c3c882a
Source dataset
uspto-grants-1977_11
Patent number
US04060540

Reaction notes

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