Hydrogen Peroxide → HCID 54285489, compound

HRID 979741Notes

Reaction equation

HRID 979741 reaction equation
[C:1]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CS(O)(=O)=[O:25].OO>C(OCC)(=O)C>[C:1]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][OH:25])=[O:21])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 6395Methanesulfonic AcidHCID 437326HCID 437326, compound

Product 1

HCID 54285489HCID 54285489, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

A 250 mL beaker was charged with 35.0 g (0.112 mol) of N-lauroyl-6-aminocaproic acid and 70 mL of 98% methanesulfonic acid. The resulting solution was cooled in an ice bath and, with stirring, 21.2 g of 90% hydrogen peroxide (19.0 g, 0.559 mol of hydrogen peroxide) was added dropwise at a rate so that the temperature of the reaction mixture did not rise above 20° C. (required 15 min.). The resulting solution was stirred at room temperature for 3 hrs., cooled to -15° C., and poured over ice. Ethyl acetate (150 mL) was added, the mixture was warmed to 60° C. in a water bath, and the water layer separated. An additional 100 mL of water was added, the solution again warmed to 60° C. and the water layer separated and discarded. The ethyl acetate solution was cooled to -15° C., and the crystals which formed were removed by filtration and washed with 2×50 mL portions of -15° C. ethyl acetate. The yield of N-lauroyl-6-aminoperoxycaproic acid was 33.1 g; analysis for available oxygen (AvO) indicated 4.31% (theoretical yield=36.9 g having an AvO of 4.86%), mp 70°-75° C.

Workup

  1. temperatureThe resulting solution was cooled in an ice bath
  2. customdid not rise above 20° C.
  3. custom15 min.
  4. stirringThe resulting solution was stirred at room temperature for 3 hrs
  5. additionpoured over ice
  6. temperaturethe mixture was warmed to 60° C. in a water bath
  7. customthe water layer separated
  8. additionAn additional 100 mL of water was added
  9. temperaturethe solution again warmed to 60° C.
  10. customthe water layer separated
  11. temperatureThe ethyl acetate solution was cooled to -15° C.
  12. customthe crystals which formed
  13. customwere removed by filtration
  14. washwashed with 2×50 mL portions of -15° C. ethyl acetate

Sources & evidence

ORD record
ord-a3608870ffbb4cf88918071b58932266
Source dataset
uspto-grants-1987_01
Patent number
US04634551

Reaction notes

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