Réaction #417899

Équation de réaction

ethylene glycol

3,5-Di-tert-butylhydroquinone

1,2-dibromoethane

potassium carbonate

→

title compound

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

Solvants

Water

Conditions de réaction

Traitement

1. 1
   Autreto quench
2. 2
   Autrethe reaction
3. 3
   Extractionthe organic compound was extracted by CH2Cl2
4. 4
   ConcentrationThe resulting solution was concentrated
5. 5
   Autreto afford a crude oil
6. 6
   AutreThe crude oil was then chromatographed (silica, hexane/ethyl acetate=20:1) mixture

Mode opératoire

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).

Source