Benzene → HCID 86739514, compound

HRID 1589530Notes

Reaction equation

HRID 1589530 reaction equation
C1C=CC=CC=1.[CH2:7]([CH2:17][C:18](=O)[CH3:19])/[CH:8]=[C:9](/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])\[CH3:10].[C:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])#[N:22].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[C:21]([CH:23]([CH:18]([CH3:19])[CH2:17][CH2:7]/[CH:8]=[C:9](\[CH3:10])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[C:24]([O:26][CH2:27][CH3:28])=[O:25])#[N:22]

Participants

6

Reactant 4

HCID 241BenzeneHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 1549778Geranylacetone

Product 1

HCID 86739514HCID 86739514, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 200 ml. of benzene was dissolved 50 g. of geranyl acetone, and then 42 g. of ethyl cyanoacetate, 6 g. of ammonium acetate and 6 g. of acetic acid were added to the solution. The mixture was then refluxed for 8 hours while removing the produced water. The reaction mixture was washed with water and dried. To this was added dropwise a solution of 5.7 g. of sodium borohydride in 40 ml. of ethanol, under stirring and at 10°-20° C. The stirring was continued for 1 hour. Then, 60 ml. of 10% acetic acid was added to the reaction mixture, and the mixture was subsequently washed with water and dried. The solvent was then removed by evaporation and the residue was purified by silica gel column chromatography to obtain 59 g. of the desired oily product.

Workup

  1. temperatureThe mixture was then refluxed for 8 hours
  2. customwhile removing the produced water
  3. washThe reaction mixture was washed with water
  4. customdried
  5. additionTo this was added dropwise a solution of 5.7 g
  6. additionof 10% acetic acid was added to the reaction mixture
  7. washthe mixture was subsequently washed with water
  8. customdried
  9. customThe solvent was then removed by evaporation
  10. customthe residue was purified by silica gel column chromatography
  11. customto obtain 59 g

Sources & evidence

ORD record
ord-18db099a1be141a6995611868b74f33e
Source dataset
uspto-grants-1986_02
Patent number
US04571408

Reaction notes

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