Isobutyraldehyde → HCID 10198123, compound

HRID 982564Notes

Reaction equation

HRID 982564 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].C(=O)C(C)C.[C:12]([O:21]CC)(=[O:20])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)(C)(C)C.C(O)C.[Pd]>[CH2:1]([CH:14]([CH2:13][C:12]([OH:21])=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]([CH3:5])[CH3:3]

Participants

7

Reactant 3

HCID 6561IsobutyraldehydeHCID 31249Diethyl SuccinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10198123HCID 10198123, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Procedure

49.4 g of potassium tert.butoxide in 350 ml of tert.butanol were stirred and heated under reflux under nitrogen. A mixture of 36.4 ml of isobutyraldehyde and 83.2 ml of diethyl succinate was added over a period of 0.25 hour and the mixture was heated under reflux for 1.5 hours. The solution was evaporated to a small volume, acidified with 2N hydrochloric acid and the evaporation was continued. The residue, diluted with water, was extracted three times with 300 ml of diethyl ether each time and the ether solutions were combined, washed with water and extracted three times with 200 ml of 10% potassium carbonate solution each time. The basic solution was acidified with concentrated hydrochloric acid and the product was extracted into diethyl ether, washed with water, dried over anhydrous magnesium sulfate and evaporated to give an oil. This oil was dissolved in 400 ml of ethanol and the solution was hydrogenated for 2 hours in the presence of 5 g of 5% palladium/carbon. After filtration and evaporation of the filtrate there were obtained 69.8 g of crude 1-ethyl hydrogen 2(RS)-isobutylsuccinate.

Workup

  1. temperatureheated
  2. temperatureunder reflux under nitrogen
  3. additionwas added over a period of 0.25 hour
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 1.5 hours
  6. customThe solution was evaporated to a small volume
  7. customthe evaporation
  8. additionThe residue, diluted with water
  9. extractionwas extracted three times with 300 ml of diethyl ether each time
  10. washwashed with water
  11. extractionextracted three times with 200 ml of 10% potassium carbonate solution each time
  12. extractionthe product was extracted into diethyl ether
  13. washwashed with water
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customevaporated
  16. customto give an oil
  17. filtrationAfter filtration and evaporation of the filtrate there

Sources & evidence

ORD record
ord-d760e864f47a4c919d905a43354da52b
Source dataset
uspto-grants-1991_02
Patent number
US04996358

Reaction notes

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