Sulfuric Acid → HCID 14329815, compound

HRID 35579Notes

Reaction equation

HRID 35579 reaction equation
[CH2:1]([CH:3]([CH:9]([N+:11]([O-:13])=[O:12])[CH3:10])[CH2:4][CH:5]([OH:8])[C:6]#[N:7])[CH3:2].S(=O)(=O)(O)[OH:15].[C:19](O)([CH3:22])([CH3:21])[CH3:20]>O>[C:19]([NH:7][C:6](=[O:15])[C:5](=[O:8])[CH2:4][CH:3]([CH2:1][CH3:2])[CH:9]([N+:11]([O-:13])=[O:12])[CH3:10])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 143297994-Ethyl-2-hydroxy-5-nitrohexanenitrile

Product 1

HCID 14329815HCID 14329815, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-ethyl-2-hydroxy-5-nitrohexane nitrile (1.7 g) in t-butanol (6.8 ml) was added conc. sulfuric acid (0.8 ml) at 0° C. with stirring. After stirring for an hour at room temperature, the mixture was heated at 75° C. for an hour. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed successively with water and brine, dried over magnesium sulfate, and then evaporated to dryness in vacuo. The resulting oil was dissolved in acetic acid (9 ml) and chromium trioxide (0.82 g) was added thereto. The resulting mixture was heated at 100° C. for 1.5 hours, with stirring, concentrated, diluted with water, and then extracted with ethyl acetate. The extract was washed successively with water and brine, and then dried over magnesium sulfate. Removal of the solvent gave an oil which was purified by a preparative thin layer chromatography (solvent: chloroform) to give N-t-butyl-4-ethyl-5-nitro-2-oxo-hexanamide (0.46 g).

Workup

  1. stirringAfter stirring for an hour at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness in vacuo
  6. dissolutionThe resulting oil was dissolved in acetic acid (9 ml)
  7. additionchromium trioxide (0.82 g) was added
  8. temperatureThe resulting mixture was heated at 100° C. for 1.5 hours
  9. stirringwith stirring
  10. concentrationconcentrated
  11. additiondiluted with water
  12. extractionextracted with ethyl acetate
  13. washThe extract was washed successively with water and brine
  14. dry with materialdried over magnesium sulfate
  15. customRemoval of the solvent
  16. customgave an oil which
  17. customwas purified by a preparative thin layer chromatography (solvent: chloroform)

Sources & evidence

ORD record
ord-98c415cedd904e65ade2eb55b658c765
Source dataset
uspto-grants-1988_08
Patent number
US04767768

Reaction notes

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