Hydrogen Peroxide → 6-Decylamino-6-oxoperoxycaproic acid

HRID 979751Notes

Reaction equation

HRID 979751 reaction equation
[C:1]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][OH:21])=[O:19])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(NC(=O)CCCCC(O)=[O:39])CCCCCCCCC.OO>CS(O)(=O)=O>[CH2:1]([NH:12][C:13](=[O:39])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][OH:21])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 190332596-Decylamino-6-oxocaproic acidHCID 54087459N-Decanoyl-6-Aminoperoxycaproic Acid

Product 1

HCID 225562336-Decylamino-6-oxoperoxycaproic acid

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
-15 °C

Procedure

6-Decylamino-6-oxoperoxycaproic acid was prepared according to the procedure described in Example I for N-decanoyl-6-aminoperoxycaproic acid. Thus, the methyl ester of 6-decylamino-6-oxocaproic acid (29.9 g, 0.10 mol), hydrogen peroxide (17.0 g, 0.50 mol), and 98% methanesulfonic acid (60 mL) were reacted at room temperature for 2 hrs., the reaction mixture poured over ice, and the peroxyacid extracted into 125 mL of 60° C. ethyl acetate. The aqueous layer was discarded and the warm ethyl acetate solution was washed with two 100 mL portions of water. The ethyl acetate solution was transferred to a 250 mL Erlenmeyer flask (rinsed with 25 mL ethyl acetate), reheated to 60° C., and then cooled to -15° C. The crystals of N-decylamino-6-oxoperoxycaproic acid were collected by filtration, washed twice with 50 mL of ice-cold ethyl acetate and air dried. Yield was 21.6 g having peroxyacid AvO of 4.49% (theoretical Yield=30.1 g of 5.32% AvO), and mp 77°-85° C.

Workup

  1. addition, the reaction mixture poured over ice
  2. extractionthe peroxyacid extracted into 125 mL of 60° C. ethyl acetate
  3. washthe warm ethyl acetate solution was washed with two 100 mL portions of water
  4. washThe ethyl acetate solution was transferred to a 250 mL Erlenmeyer flask (rinsed with 25 mL ethyl acetate)
  5. customreheated to 60° C.
  6. filtrationThe crystals of N-decylamino-6-oxoperoxycaproic acid were collected by filtration
  7. washwashed twice with 50 mL of ice-cold ethyl acetate and air
  8. customdried

Sources & evidence

ORD record
ord-27d21926e4094e9983eb5d3bbb2772a6
Source dataset
uspto-grants-1987_01
Patent number
US04634551

Reaction notes

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