Acetic Acid → HCID 86739514, compound

HRID 1263235Notes

Reaction equation

HRID 1263235 reaction equation
[CH2:1]([CH2:11][C:12](=O)[CH3:13])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:16].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1>[C:15]([CH:17]([CH:12]([CH3:13])[CH2:11][CH2:1]/[CH:2]=[C:3](\[CH3:4])/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 1549778Geranylacetone

Product 1

HCID 86739514HCID 86739514, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 200 ml of benzene was dissolved 50 g of geranylacetone, and 42 g of ethyl cyanoacetate, and then 6 g of ammonium acetate and 6 g of acetic acid were added to the solution. The mixture was refluxed for 8 hours while removing the water formed by the reaction. The liquid reaction mixture was washed with water and dried, and a solution of 5.7 g of sodium borohydride in 40 ml of ethanol was added dropwise to the liquid reaction mixture at 10° to 20° C. under agitation. The mixture was stirred for 1 hour and 60 ml of 10% acetic acid was added to the liquid reaction mixture. Then, the mixture was washed with water and dried, and the solvent was removed by distillation and the residue was purified by column chromatography using silica gel to obtain 59 g of the intended compound in the form of an oil.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. customwhile removing the water
  3. customformed by the reaction
  4. customThe liquid reaction mixture
  5. washwas washed with water
  6. customdried
  7. additiona solution of 5.7 g of sodium borohydride in 40 ml of ethanol was added dropwise to the liquid reaction mixture at 10° to 20° C. under agitation
  8. addition60 ml of 10% acetic acid was added to the liquid reaction mixture
  9. washThen, the mixture was washed with water
  10. customdried
  11. customthe solvent was removed by distillation
  12. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-859e5f448f0b40648821674a5dece86b
Source dataset
uspto-grants-1984_06
Patent number
US04456603

Reaction notes

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