Sulfuric Acid → 2,6-DIMETHYL-2,6-bis(t-BUTYLPEROXY)-4-HEPTANONE

HRID 1577968

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].S(=O)(=O)(O)O>CCCCC>[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

Conditions

Temperature: 10 °C

Procedure

A mixture of 6.9 g. (0.05 mole) of phorone and 23.2 g. (0.2 mole) of anhydrous 81% t-butyl hydroperoxide was diluted with 50 ml of pentane and the mixture stirred at 10° C., while 5.7 g. of 77% sulfuric acid solution was slowly added over at thirty minute time period. The mixture was then allowed to warm slowly to 25° C. and stirred for 72 hours. After the reaction mixture was washed with water and sodium bisulfite solution, it was dried over anhydrous magnesium sulfate, the drying agent separated and the pentane removed under reduced pressure. The product weighed 11.4 g. (71.7% of the calculated amount). The infrared spectrum showed a strong absorption in the 880 cm-1 region, usually associated with t-butylperoxy groups and no absorption in the regions ascribed to hydroxyl or olefin. A GLC scan showed one large major peak for the expected product. By active oxygen assay, the purity of the product was estimated at 93%.

Workup

additionA mixture of 6.9 g
temperatureto warm slowly to 25° C.
stirringstirred for 72 hours
washAfter the reaction mixture was washed with water and sodium bisulfite solution, it
dry with materialwas dried over anhydrous magnesium sulfate
customthe drying agent separated
customthe pentane removed under reduced pressure
customa strong absorption in the 880 cm-1 region
customno absorption in the regions

Sources & evidence

ORD record: ord-e8fdb20c43174ffdbe6f79e117db83e3
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04289914

Linked notes

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