Hydrochloric Acid → (E, E)-3,7,11,15-Tetramethyl-6,10,14-hexadecatrienonitrile

HRID 1979539Notes

Reaction equation

HRID 1979539 reaction equation
[C:1]([CH:3]([CH:9]([CH3:26])[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:25])/[CH2:14][CH2:15]/[CH:16]=[C:17](\[CH3:24])/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])C(OCC)=O)#[N:2].[OH-].[Na+].C(O)C(O)C.Cl>>[CH3:26][CH:9]([CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:25])/[CH2:14][CH2:15]/[CH:16]=[C:17](\[CH3:24])/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH2:3][C:1]#[N:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1030Propylene GlycolHCID 14798Sodium HydroxideHCID 15589936ethyl (E,E)-2-cyano-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoate

Product 1

HCID 11414994(E, E)-3,7,11,15-Tetramethyl-6,10,14-hexadecatrienonitrile

Procedure

To the entirety of the product obtained in the above (a) step, there were added 29 g. of sodium hydroxide and 100 ml. of propylene glycol, and the mixture was stirred at room temperature for 10 min. The reaction mixture was made acidic by addition of 6N hydrochloric acid, and was then extracted with benzene. The extract was then washed with water and dried. The solvent was then removed by evaporation. The obtained oily product was dissolved in 100 ml. of pyridine, and the resulting solution was refluxed for 2 hours after addition of 0.5 g. of copper powder. Subsequently, the copper powder was removed by filtration and the solvent was removed by evaporation. The residue was dissolved in n-hexane, washed with water and dried. The solvent was then removed by evaporation and the residue was purified by silica gel column chromatography to obtain 34 g. of the desired oily product.

Workup

  1. additionwere added 29 g
  2. extractionwas then extracted with benzene
  3. washThe extract was then washed with water
  4. customdried
  5. customThe solvent was then removed by evaporation
  6. dissolutionThe obtained oily product was dissolved in 100 ml
  7. temperatureof pyridine, and the resulting solution was refluxed for 2 hours
  8. additionafter addition of 0.5 g
  9. customSubsequently, the copper powder was removed by filtration
  10. customthe solvent was removed by evaporation
  11. dissolutionThe residue was dissolved in n-hexane
  12. washwashed with water
  13. customdried
  14. customThe solvent was then removed by evaporation
  15. customthe residue was purified by silica gel column chromatography
  16. customto obtain 34 g

Sources & evidence

ORD record
ord-aece9026b7584354a601aeb492dcde8d
Source dataset
uspto-grants-1984_11
Patent number
US04481217

Reaction notes

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