Reaction #417899

Reaction equation

ethylene glycol

3,5-Di-tert-butylhydroquinone

1,2-dibromoethane

potassium carbonate

→

title compound

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

Solvents

Water

Conditions

Workup

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

Procedure

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