Oxygen → t-Butyl O-p-Tolyl Monoperoxyglutarate

HRID 65896Notes

Reaction equation

HRID 65896 reaction equation
[C:1]([O:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:9]1([CH3:24])[CH:14]=[CH:13][C:12]([O:15][C:16]([CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22])=[O:17])=[CH:11][CH:10]=1.O=O>C(OCC)C>[C:21]([O:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:22])[CH2:20][CH2:19][CH2:18][C:16]([O:15][C:12]1[CH:11]=[CH:10][C:9]([CH3:24])=[CH:14][CH:13]=1)=[O:17]

Participants

6

Reactant 4

HCID 977OxygenHCID 6410tert-Butyl hydroperoxideHCID 14798Sodium HydroxideHCID 22756218HCID 22756218, compound

Product 1

HCID 22756236t-Butyl O-p-Tolyl MonoperoxyglutarateYield 76.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a vigorously stirred solution of 4.9 g. (0.045 mole) of 82.0% t-butyl hydroperoxide and 18.0 g. (0.045 mole) of aqueous 10% sodium hydroxide at 10°-14° C. was slowly added 8.2 g. (0.034 mole) of 4-(p-tolyloxycarbonyl)butyryl chloride (prepared from p-tolyl 4-carboxybutyrate and thionyl chloride) in 25 ml. of diethyl ether. The reaction mixture was then stirred for 3.5 hours at 8°-10° C. After a work-up similar to that in Example I 8.2 g. (theory, 10.0 g.) of white solid, m.p. 50°-55° C., was obtained. The assay according to "active oxygen" content was 93.6% and the corrected yield was 76.7%.

Workup

  1. customat 10°-14° C.
  2. custom(theory, 10.0 g.) of white solid, m.p. 50°-55° C., was obtained

Sources & evidence

ORD record
ord-8d1dc8d005d94d159f291dd22ef40a48
Source dataset
uspto-grants-1978_12
Patent number
US04129586

Reaction notes

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