Benzene → ethyl (E,E)-2-cyano-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoate

HRID 1979538Notes

Reaction equation

HRID 1979538 reaction equation
C1C=CC=CC=1.[CH2:7]([CH2:22][C:23](=O)[CH3:24])[CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH3:15])[CH3:10].[C:26]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])#[N:27].C([O-])(=O)C.[NH4+]>O.C(O)(=O)C>[C:26]([CH:28]([CH:23]([CH3:24])[CH2:22][CH2:7]/[CH:8]=[C:9](\[CH3:10])/[CH2:11][CH2:12]/[CH:13]=[C:14](\[CH3:15])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[C:29]([O:31][CH2:32][CH3:33])=[O:30])#[N:27]

Participants

7

Reactant 4

HCID 241BenzeneHCID 7764Ethyl cyanoacetateHCID 612065,9,13-Pentadecatrien-2-one, 6,10,14-trimethyl-HCID 517165Ammonium Acetate

Product 1

HCID 15589936ethyl (E,E)-2-cyano-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 200 ml. of benzene was dissolved 50 g. of farnesyl acetone, and then 28 g. of ethyl cyanoacetate, 5 g. of ammonium acetate and 5 g. of acetic acid were added to the solution. The mixture was then refluxed for 8 hours with removal of the produced water. The reaction mixture then was washed with water and dried. To this mixture there was added dropwise a solution of 4.3 g. of sodium borohydride in 50 ml. of ethanol, under stirring and at 10°-20° C. The stirring was continued for 1 hour. Then, 50 ml. of 10% acetic acid was added to the reaction mixture, and the mixture was subsequently washed with water and dried. The solvent was removed by evaporation and then the residue was purified by silica gel column chromatography to obtain 50.5 g. of the desired oily product.

Workup

  1. washThe reaction mixture then was washed with water
  2. customdried
  3. additionTo this mixture there was added dropwise a solution of 4.3 g
  4. additionof 10% acetic acid was added to the reaction mixture
  5. washthe mixture was subsequently washed with water
  6. customdried
  7. customThe solvent was removed by evaporation
  8. customthe residue was purified by silica gel column chromatography
  9. customto obtain 50.5 g

Sources & evidence

ORD record
ord-871859d79d5b46e2b5e184792751a58e
Source dataset
uspto-grants-1984_11
Patent number
US04481217

Reaction notes

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