Hydrochloric Acid → (E,E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoic acid

HRID 1979540Notes

Reaction equation

HRID 1979540 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:3][C:4]#N.[OH-:22].[K+].C(O)C([OH:27])C.Cl>O>[CH3:1][CH:2]([CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:3][C:4]([OH:27])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1030Propylene GlycolHCID 14797Potassium HydroxideHCID 11414994(E, E)-3,7,11,15-Tetramethyl-6,10,14-hexadecatrienonitrile

Product 1

HCID 12837064(E,E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 34 g. of the product obtained in the above (b) step, there were added 23 g. of potassium hydroxide, 10 ml. of water and 70 ml. of propylene glycol, and the mixture was stirred at 130° C. for 7 hours. The reaction mixture was made acidic by addition of hydrochloric acid, and was then extracted with n-hexane. The extract was washed with water and dried, and the solvent was removed by evaporation. The residue was purified by silica gel column chromatography to obtain 30 g. of the desired oily product.

Workup

  1. additionwere added 23 g
  2. extractionwas then extracted with n-hexane
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain 30 g

Sources & evidence

ORD record
ord-a0728fe71f3c4a7581bd9de87cc0131f
Source dataset
uspto-grants-1984_11
Patent number
US04481217

Reaction notes

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