Reaktion #52034

Reaktionsgleichung

3,4-di-n-propoxythiophene

1,2,6-hexanetriol

p-toluenesulphonic acid

→

4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)-1-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONDuring this time, 5.8 g of distillate (substantially n-propanol) were collected
2. 2
   workup.ADDITIONThe cooled liquid was diluted with 50 ml of methylene chloride
3. 3
   Waschenwashed to neutrality
4. 4
   Trocknenthe organic phase was dried over Na2SO4
5. 5
   FiltrationAfter filtering
6. 6
   Sonstigeevaporating the methylene chloride

Vorschrift

9.06 g (45.2 mmol) of 3,4-di-n-propoxythiophene, 30.3 g (226 mmol) of 1,2,6-hexanetriol and 0.09 g (0.5 mmol) of p-toluenesulphonic acid are heated to 150 to 165° C. (bath temperature) under N2 for 3 h. During this time, 5.8 g of distillate (substantially n-propanol) were collected. The cooled liquid was diluted with 50 ml of methylene chloride, washed to neutrality and to free it of hexanetriol with water and the organic phase was dried over Na2SO4. After filtering and evaporating the methylene chloride, the residue (6.73 g=74.8% of theory) was identified by 1H NMR spectroscopy (in CDCl3 against TMS) using δ=6.30 ppm (2H, thiophene H) and 2.85 ppm (1H, OH) as being substantially 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)-1-butanol.

Quelle