Ethanol → trans Ethyl 11-ethoxy-3,7,11-trimethyldodeca-2,4-dienoate

HRID 918314Notes

Reaction equation

HRID 918314 reaction equation
[CH2:1]([OH:3])[CH3:2].[CH3:4][C:5](/[CH:12]=[CH:13]/[CH2:14][CH:15]([CH3:22])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[OH-].[K+].[BH4-].[Na+]>O>[CH2:1]([O:3][C:19]([CH3:20])([CH3:21])[CH2:18][CH2:17][CH2:16][CH:15]([CH3:22])[CH2:14]/[CH:13]=[CH:12]/[C:5]([CH3:4])=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 702Ethanol3×HCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 86733725trans Ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate

Product 1

HCID 86733726trans Ethyl 11-ethoxy-3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fifteen grams of mercuric acetate in 50 ml. of dry ethanol is added to 12 g. of trans ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate in 30 ml. of dry ethanol cooled in an ice bath. The temperature is allowed to come to room temperature by standing overnight. Then the mixture is cooled to 0°, 10 g. of potassium hydroxide in 150 ml. of ethanol is added followed by addition of 1.0 g. of sodium borohydride in small portions. After about 30 minutes at 0°, water is added and mixture left at room temperature for 2 hours. The mixture is filtered, filtrate concentrated and extracted with ether. The ethereal extract is washed, dried, and evaporated to yield trans ethyl 11-ethoxy-3,7,11-trimethyldodeca-2,4-dienoate which is purified by distillation or chromatography.

Workup

  1. customto come to room temperature
  2. temperatureThen the mixture is cooled to 0°
  3. additionfollowed by addition of 1.0 g
  4. waitAfter about 30 minutes at 0°
  5. waitmixture left at room temperature for 2 hours
  6. filtrationThe mixture is filtered
  7. concentrationfiltrate concentrated
  8. extractionextracted with ether
  9. extractionThe ethereal extract
  10. washis washed
  11. customdried
  12. customevaporated

Sources & evidence

ORD record
ord-2a1451b7b3984e92b3a7b30d87edd834
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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