Реакция #417899

Уравнение реакции

ethylene glycol

3,5-Di-tert-butylhydroquinone

1,2-dibromoethane

potassium carbonate

→

title compound

5,7-di-tert-butyl-1,4-benzodioxin

Растворители

Water

Условия реакции

Обработка

1. 1
   Другоеto quench
2. 2
   Другоеthe reaction
3. 3
   Экстракцияthe organic compound was extracted by CH2Cl2
4. 4
   КонцентрированиеThe resulting solution was concentrated
5. 5
   Другоеto afford a crude oil
6. 6
   ДругоеThe crude oil was then chromatographed (silica, hexane/ethyl acetate=20:1) mixture

Методика

3,5-Di-tert-butylhydroquinone (3.33 g, 15 mmol) was combined with 1,2-dibromoethane (5.6 g), potassium carbonate (4.35 g) and ethylene glycol (25 mL). The mixture was heated in a 120° C. oil bath under an Ar atmosphere for 12 h. Water was added to the reaction mixture to quench the reaction and then the organic compound was extracted by CH2Cl2. The resulting solution was concentrated to afford a crude oil. The crude oil was then chromatographed (silica, hexane/ethyl acetate=20:1) mixture to afford the title compound (Rf=0.5, 5:1 hexane/ethyl acetate). 1H NMR (500 MHz, CDCl3): δ 7.03 (d, J=2 Hz, 1H), 6.93 (d, J=2 Hz, 1H), 4.34 (s, 4H), 1.53 (s, 9H), 1.43 (s, 9H).

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