Reaktion #160652

Reaktionsgleichung

HCl

1,6-bis(4-formylphenoxy)hexane

1,3-propanedithiol

HCl

→

1,6-bis[4-(1,3-dithian-2-yl)phenoxy]hexane

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturreflux cooler, internal thermometer and magnetic stirrer
2. 2
   workup.STIRRINGthe reaction mixture was stirred for another 30 min
3. 3
   Temperaturcooling
4. 4
   Sonstigethe ice bath was removed
5. 5
   workup.STIRRINGthe red-brown suspension was stirred for a further 2 h at room temperature
6. 6
   workup.DISTILLATIONThe solvent was then distilled off with a membrane pump (400 to 10 mbar) into a cold trap
7. 7
   workup.ADDITION300 ml ethyl acetate and 100 ml methanol added to the residue
8. 8
   workup.STIRRINGthe reaction mixture stirred
9. 9
   FiltrationThe suspension was filtered
10. 10
    Waschenthe solid residue washed with 100 ml methanol and 100 ml acetone
11. 11
    Sonstigedried to constant weight in the vacuum
12. 12
    Sonstigedrying cupboard

Vorschrift

A suspension of 52.55 g (0.16 mol) 1,6-bis(4-formylphenoxy)hexane, 200 ml chloroform and 34.85 g (0.32 mol) 1,3-propanedithiol was stirred in a 500-ml three-necked flask with gas-entry tube, reflux cooler, internal thermometer and magnetic stirrer and cooled to −10° C. Dry HCl gas was introduced for approx. 15 min, whereupon the suspension thickened markedly. After the introduction of the HCl was complete, the reaction mixture was stirred for another 30 min accompanied by ice-cooling, the ice bath was removed and the red-brown suspension was stirred for a further 2 h at room temperature. The solvent was then distilled off with a membrane pump (400 to 10 mbar) into a cold trap, 300 ml ethyl acetate and 100 ml methanol added to the residue and the reaction mixture stirred. The suspension was filtered, the solid residue washed with 100 ml methanol and 100 ml acetone and dried to constant weight in the vacuum drying cupboard. 78.2 g (96% of the theoretical value) 1,6-bis[4-(1,3-dithian-2-yl)phenoxy]hexane was obtained as a reddish, poorly soluble solid (m.p.: 189-192° C.).

Quelle