Reaktion #2027

Reaktionsgleichung

1,3-Dibromopropane

sodium sulfite

Norit

→

title compound

Ausbeute 85.6%

Sodium 1,3-propanedisulfonate

Ausbeute 85.6%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis compound was prepared by a modification of the method
2. 2
   Temperaturat reflux temperature for 48 h
3. 3
   SonstigeInorganic salts (sodium bromide and sodium sulfite) were removed by successive treatment of the resultant
4. 4
   Sonstigereaction mixture with barium hydroxide and silver(I) oxide
5. 5
   SonstigeBarium ions were removed by treatment of the aqueous solution with Amberlite-120 (sodium form) ion-exchange resin
6. 6
   SonstigeThe solvent was removed on a rotary evaporator
7. 7
   Sonstigethe crude product was recrystallized from water-ethanol several times

Vorschrift

This compound was prepared by a modification of the method described in Stone, G. C. H. (1936) J. Am. Chem. Soc., 58:488. 1,3-Dibromopropane (40.4 g, 0.20 mol) was treated with sodium sulfite (60.3 g, 0.50 mol) in water at reflux temperature for 48 h. Inorganic salts (sodium bromide and sodium sulfite) were removed by successive treatment of the resultant reaction mixture with barium hydroxide and silver(I) oxide. The solution was then neutralized with Amberlite-120 (acid form) and decolorized with Norit-A. Barium ions were removed by treatment of the aqueous solution with Amberlite-120 (sodium form) ion-exchange resin. The solvent was removed on a rotary evaporator, and the crude product was recrystallized from water-ethanol several times to give the title compound (42.5 g). The small amount of trapped ethanol was removed by dissolving the crystals in a minimum amount of water and then concentrating the solution to dryness. The pure product was further dried under high vacuum at 56° C. for 24 h: mp>300° C.; 1H NMR (D2O) δ: 3.06-3.13 (m, 4H, H-1 and H-3), 2.13-2.29 (m, 2H, H-2); 13C NMR (D2O) δ: 52.3 (C-1 and C-3), 23.8 (C-2).

Quelle