Ethanol → HCID 53777000, compound

HRID 2164187Notes

Reaction equation

HRID 2164187 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])=[CH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[OH-].[K+].[BH4-].[Na+].[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:2]([CH3:1])=[CH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH3:20]

Participants

5

Reactant 4

HCID 702Ethanol3×HCID 14797Potassium HydroxideHCID 5497503,7-Nonadienoic acid, 4,8-dimethyl-, methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 53777000HCID 53777000, compound

Procedure

To a solution of 1.7 g. of methyl 4,8-dimethylnona-3,7-dienoate in 20 ml. of ethanol, cooled to about 0°, is added a suspension of 2.3 g. of mercuric acetate in 50 ml. of ethanol, over about 15 minutes. The reaction mixture is stirred for two hours and then, with cooling, 1.2 g. of potassium hydroxide in 20 ml. of ethanol is added. Then 0.26 g. of sodium borohydride is added in small portions and stirring continued 30 minutes. The solution is decanted, concentrated to half volume, diluted with water and extracted with ether. The ethereal phase is washed with water, dried over magnesium sulfate and the product chromatographed to yield methyl 8-ethoxy-4,8-dimethylnon-3-enoate.

Workup

  1. additionis added
  2. additiona suspension of 2.3 g
  3. temperaturewith cooling
  4. stirringstirring continued 30 minutes
  5. customThe solution is decanted
  6. concentrationconcentrated to half volume
  7. additiondiluted with water
  8. extractionextracted with ether
  9. washThe ethereal phase is washed with water
  10. dry with materialdried over magnesium sulfate
  11. customthe product chromatographed

Sources & evidence

ORD record
ord-98be0f7d26864c598c23f876d7df0893
Source dataset
uspto-grants-1979_01
Patent number
US04137273

Reaction notes

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