Ethanol → 1-Iodo-trans-1-octene-3-ol

HRID 436101Notes

Reaction equation

HRID 436101 reaction equation
[I:1]/[CH:2]=[CH:3]/[C:4](=[O:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(O)C.[BH4-].[Na+]>O>[I:1]/[CH:2]=[CH:3]/[CH:4]([OH:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 4311764Sodium borohydrideHCID 11139597(E)-1-Iodo-1-octen-3-one

Product 1

HCID 110432831-Iodo-trans-1-octene-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 78.2 g. (0.310 moles) of 1-iodo-trans-1-octen-3-one (Example 724) in 150 ml. of absolute ethanol is added dropwise over 2 hours to a slurry of 6.49 g. (0.172 moles) of sodium borohydride in 50 ml. of absolute ethanol cooled in an ice bath. After the addition is complete, the mixture is stirred for 2 hours with ice cooling and is then poured into 1 l. of water. The mixture is extracted into benzene and the organic phase is washed with saturated brine, dried (Na2SO4) and evaporated. The resulting oil is dissolved into 400 ml. of absolute ethanol and treated with 5 mole percent of p-carboxyphenylhydrazine at 70° C. for 1.5 hours to remove residual ketone. The mixture is cooled and evaporated and the residue is dissolved into 400 ml. of ether and is filtered. The filtrate is washed with dilute sodium bicarbonate solution and saturated brine, dried (Na2SO4), and evaporated to an oil. This oil is chromatographyed upon 2 Kg. of Florisil packed in hexane and the product is obtained upon elution with benzene Distillation of the product yields a colorless oil, b.p. 74°-76° C. (0.005 tor.).

Workup

  1. additionAfter the addition
  2. additionis then poured into 1 l
  3. extractionThe mixture is extracted into benzene
  4. washthe organic phase is washed with saturated brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. dissolutionThe resulting oil is dissolved into 400 ml
  8. additionof absolute ethanol and treated with 5 mole percent of p-carboxyphenylhydrazine at 70° C. for 1.5 hours
  9. customto remove residual ketone
  10. temperatureThe mixture is cooled
  11. customevaporated
  12. dissolutionthe residue is dissolved into 400 ml
  13. filtrationof ether and is filtered
  14. washThe filtrate is washed with dilute sodium bicarbonate solution and saturated brine
  15. dry with materialdried (Na2SO4)
  16. customevaporated to an oil
  17. customthe product is obtained upon elution with benzene Distillation of the product
  18. customyields a colorless oil, b.p. 74°-76° C. (0.005 tor.)

Sources & evidence

ORD record
ord-c4e4f79f7c7541d09589eaebed505d31
Source dataset
uspto-grants-1977_02
Patent number
US04007210

Reaction notes

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