Hydrogen Peroxide → HCID 14574132, compound

HRID 2352141Notes

Reaction equation

HRID 2352141 reaction equation
[C:1]([CH:9]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:10][C:11](O)=[O:12])([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].CS(O)(=O)=[O:21].[OH:24][OH:25]>>[C:1]([CH:9]([CH2:14][CH2:15][C:16]([O:18][OH:21])=[O:17])[CH2:10][C:11]([O:24][OH:25])=[O:12])([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 6395Methanesulfonic AcidHCID 145741293-(2,4,4-Trimethylpentan-2-yl)hexanedioic acid

Product 1

HCID 14574132HCID 14574132, compound

Procedure

β-t-octyladipic acid (86.1 g, 0.33 mol) was powdered using a mortar and pestle and added to a beaker containing 98% methanesulfonic acid. The resultant suspension was cooled to 20° C. and 70% hydrogen peroxide was added slowly with constant stirring to maintain the temperature just below 40° C. After the addition was complete (about one-half hour) the suspension was stirred at room temperature for 1 hour after which the resultant clear solution was poured into 500 ml of cold distilled water, and extracted with dichloromethane (3×100 ml). The dichloromethane solution was washed with distilled water (2×50 ml), dried over anhydrous magnesium sulfate after which the solvent was removed on a rotary evaporator to provide a clear oil. Storage of the oil in a stoppered flask overnight at 0.5° C. resulted in crystallization of β-t-octyldiperoxyadipic acid as a white brittle solid (83.4 g,; mp 60°-62° C.; % AvO=9.3, theory 11.0; HPLC, C18ODS column, 70% methanol solent, retention time: 6.3 min., diperoxy-acid, relative peak area 76%; 7.4 min, monoperoxyacid, relative peak area 24%.

Workup

  1. additionadded to a beaker
  2. temperatureto maintain the temperature just below 40° C
  3. additionAfter the addition
  4. custom(about one-half hour)
  5. stirringwas stirred at room temperature for 1 hour after which the resultant clear solution
  6. additionwas poured into 500 ml
  7. distillationof cold distilled water
  8. extractionextracted with dichloromethane (3×100 ml)
  9. washThe dichloromethane solution was washed with distilled water (2×50 ml)
  10. dry with materialdried over anhydrous magnesium sulfate after which the solvent
  11. customwas removed on a rotary evaporator
  12. customto provide a clear oil

Sources & evidence

ORD record
ord-cc82191e98924e329ea51d65bfd727ff
Source dataset
uspto-grants-1989_10
Patent number
US04876046

Reaction notes

Loading…