Oxygen → t-Butyl O-p-Tolyl Monoperoxysuccinate

HRID 65895Notes

Reaction equation

HRID 65895 reaction equation
[C:1]([O:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:9]1([CH3:23])[CH:14]=[CH:13][C:12]([O:15][C:16]([CH2:18][CH2:19][C:20](Cl)=[O:21])=[O:17])=[CH:11][CH:10]=1.O=O>CCOCC>[C:20]([O:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:21])[CH2:19][CH2:18][C:16]([O:15][C:12]1[CH:11]=[CH:10][C:9]([CH3:23])=[CH:14][CH:13]=1)=[O:17]

Participants

6

Reactant 4

HCID 977OxygenHCID 6410tert-Butyl hydroperoxideHCID 14798Sodium HydroxideHCID 227562303-(p-Tolyloxycarbonyl)propionyl chloride

Product 1

HCID 22756226t-Butyl O-p-Tolyl MonoperoxysuccinateYield 92.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a vigorously stirred solution of 15.6 g. (0.143 mole) of 82.0% t-butyl hydroperoxide and 57.0 g. (0.143 mole) of aqueous 10% sodium hydroxide at 5°-10° C. was added slowly 24.6 g. (0.109 mole) of 3-(p-tolyloxycarbonyl)propionyl chloride (prepared from p-tolyl 3-carboxypropionate and thionyl chloride) in 50 ml. of diethyl ether. The reaction mixture was then stirred at 5°-10° C. for 3 hours, after which additional ether was added to the mixture and the resulting ether solution was washed, first with 10% sodium hydroxide solution, and finally with water until the solution was neutral. After drying over anhydrous MgSO4 and removal of the ether in vacuo 28.2 g. (theory, 30.4 g.) of white solid, m.p. 72°-77° C., was obtained. The assay according to "active oxygen" content was 100% and the corrected yield was 92.8%.

Workup

  1. washthe resulting ether solution was washed, first with 10% sodium hydroxide solution
  2. dry with materialAfter drying over anhydrous MgSO4 and removal of the ether in vacuo 28.2 g
  3. custom(theory, 30.4 g.) of white solid, m.p. 72°-77° C., was obtained

Sources & evidence

ORD record
ord-c0ea7a63904b4208a7358325c5e032b5
Source dataset
uspto-grants-1978_12
Patent number
US04129586

Reaction notes

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