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

HRID 2420413Notes

Reaction equation

HRID 2420413 reaction equation
[BH4-].[Na+].[Br:3]/[CH:4]=[CH:5]/[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl/C=C/C(=O)CCCCC>C(O)C>[Br:3]/[CH:4]=[CH:5]/[CH:6]([OH:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 110410031-Chloro-trans-1-octen-3-oneHCID 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 14.29 g. (0.378 mole) of sodium borohydride in 400 ml. of anhydrous ethanol is added the crude 1-bromo-trans-1-octen-3-one (Example 725), from 0.424 mole of 1-chloro-trans-1-octen-3-one) over 30 minutes. 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. Fractional distillation yields the title compound as a colorless oil, b.p. 66°-68° C. (0.025 torr).

Workup

  1. additionmixture of 14.29 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. distillationFractional distillation

Sources & evidence

ORD record
ord-a26ac1a9a7214360948410447f96e638
Source dataset
uspto-grants-1978_08
Patent number
US04110368

Reaction notes

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