Reaktion #215047

Reaktionsgleichung

mesityl oxide

2,5-dimethyl-2,5-dihydroperoxy-3-hexyne

sulfuric acid

→

product

Ausbeute 66.7%

2,15-DIOXO-4,4,7,7,10,10,13,13-OCTAMETHYL-5,6,11,12-TETRAOXA-8-HEXADECYNE

Ausbeute 66.7%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 19.6 g
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with water, 5% sodium hydroxide solution and again with water to pH 8
4. 4
   workup.DISTILLATIONThe mixture was then subjected to steam distillation in the presence of sodium bicarbonate solution at 20 torr for 2 hours
5. 5
   Sonstigeto remove unreacted mesityl oxide and hydroperoxide
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Sonstigethe ether removed under reduced pressure
8. 8
   Sonstigeleaving 20.52 g

Vorschrift

A mixture of 19.6 g. (0.2 mole) of mesityl oxide, 74.4 g. (0.083 mole) of 2,5-dimethyl-2,5-dihydroperoxy-3-hexyne and 60 ml. of ether was stirred at 0° C. while 1.3 g. of 77% sulfuric acid solution was slowly added. The reaction mixture was allowed to warm slowly to 30° C. and stirred for a total of 16 hours. The organic layer was separated, washed with water, 5% sodium hydroxide solution and again with water to pH 8. The mixture was then subjected to steam distillation in the presence of sodium bicarbonate solution at 20 torr for 2 hours to remove unreacted mesityl oxide and hydroperoxide. The product was taken up in ether, dried over anhydrous magnesium sulfate and the ether removed under reduced pressure leaving 20.52 g. of product (66.7% yield).

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