[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]
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 three 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%.
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