Reaction equation
[CH3:1][C:2](=[CH:4][C:5](=[O:10])[CH:6]=[C:7]([CH3:9])[CH3:8])[CH3:3].[C:11]([O:15][OH:16])([CH3:14])([CH3:13])[CH3:12]>>[CH3:1][C:2]([O:16][O:15][C:11]([CH3:14])([CH3:13])[CH3:12])([CH2:4][C:5](=[O:10])[CH2:6][C:7]([CH3:9])([O:16][O:15][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:8])[CH3:3]Participants
Procedure
A mixture of 47.0 g. (0.34 mole) of phorone and 157 g (1.36 mole) of 78% t-butyl hydroperoxide was stirred with 34 g. of dry Amberlyst 15® sulfonic acid type ion exchange resin in a 500 ml flask equipped with a condenser and thermometer for forty-eight hours at 40° C. and one hour at 50° C. The ion exchange resin was separated by filtration and the product diluted with pentane. The pentane solution was washed with water, sodium bisulfite solution, 5% sodium hydroxide solution and water. After drying over anhydrous magnesium sulfate, the pentane was removed under reduced pressure. The recovered product weighed 74.2 g. (68.5% of the calculated amount). A GLC scan showed a large major peak for the expected product. In the infrared spectrum, small bands for hydroxyl and olefin were observed but the band in the 880 cm-1 region usually associated with t-butyl peroxy groups was strong. By active oxygen assay, the purity of the product was estimated at 83%.
Workup
- additionA mixture of 47.0 g
- customThe ion exchange resin was separated by filtration
- additionthe product diluted with pentane
- washThe pentane solution was washed with water, sodium bisulfite solution, 5% sodium hydroxide solution and water
- dry with materialAfter drying over anhydrous magnesium sulfate
- customthe pentane was removed under reduced pressure
Sources & evidence
- ORD record
- ord-5ecc00f42a2a4c938363260afe89befc
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04257985
Linked notes
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