Reacción #417899

Ecuación de reacción

ethylene glycol

3,5-Di-tert-butylhydroquinone

1,2-dibromoethane

potassium carbonate

→

title compound

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

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto quench
2. 2
   Otrothe reaction
3. 3
   Extracciónthe organic compound was extracted by CH2Cl2
4. 4
   ConcentraciónThe resulting solution was concentrated
5. 5
   Otroto afford a crude oil
6. 6
   OtroThe crude oil was then chromatographed (silica, hexane/ethyl acetate=20:1) mixture

Procedimiento

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).

Fuente