Hydrogen Peroxide → 4-(Nonylamino)-4-oxobutaneperoxoic acid

HRID 1788883Notes

Reaction equation

HRID 1788883 reaction equation
[CH2:1]([NH:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[OH:18]O>CS(O)(=O)=O>[CH2:1]([NH:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([O:16][OH:18])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 454082Butanoic acid, 4-(nonylamino)-4-oxo-

Product 1

HCID 219104664-(Nonylamino)-4-oxobutaneperoxoic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
-15 °C

Procedure

A 500 mL beaker was charged with 50.0 g (0.205 mol) of 4-nonylamino-4-oxobutyric acid and 100 mL of 98% methanesulfonic acid. The resulting solution was cooled in an ice bath and, with stirring, 38.8 g of 90% hydrogen peroxide (34.9 g, 1.03 mol of hydrogen peroxide) was added dropwise at a rate such that the temperature of the reaction mixture did not rise above 20° C. (required 10 minutes). The solution was stirred at room temperature for 1.5 hours, cooled to -15° C., and poured over ice. The precipitated solid was collected by filtration and washed with water. The filter cake was reslurried with water, filtered, and washed with water. The wet filter cake was dissolved in 250 mL of 60° C. ethyl acetate, the water layer removed with a pipet, and the ethyl acetate solution cooled to -15° C. The crystals which formed were collected by filtration, washed with -15° C. ethyl acetate, and air dried to yield 47.5 g of 4-nonylamino-4-oxoperoxybutyric acid (1), mp 85°-91° C., analysis for available oxygen (AvO)=5.61%. Theoretical yield=53.2 g having an AvO of 6.17%.

Workup

  1. temperatureThe resulting solution was cooled in an ice bath
  2. customdid not rise above 20° C.
  3. custom10 minutes
  4. stirringThe solution was stirred at room temperature for 1.5 hours
  5. additionpoured over ice
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water
  8. filtrationfiltered
  9. washwashed with water
  10. dissolutionThe wet filter cake was dissolved in 250 mL of 60° C. ethyl acetate
  11. customthe water layer removed with a pipet
  12. temperaturethe ethyl acetate solution cooled to -15° C
  13. customThe crystals which formed
  14. filtrationwere collected by filtration
  15. washwashed with -15° C. ethyl acetate, and air
  16. customdried

Sources & evidence

ORD record
ord-dfb6c7d8e04e492d834e68ed06daa65a
Source dataset
uspto-grants-1987_08
Patent number
US04686063

Reaction notes

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