Reaktion #43891

Reaktionsgleichung

H2SO4

tetrabutylammonium hydroxide

1-naphthalenesulfonyl chloride

Na2SO3

NaHCO3

→

Tetrabutylammonium 1-Naphthalene Sulfinate

Lösungsmittel

methanol

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   Temperaturwas then further cooled in a refrigerator
3. 3
   Sonstigeresulted in the formation of a precipitate
4. 4
   ExtraktionThe mixture was extracted three times with 100 mL of ethyl acetate
5. 5
   Sonstigethe solvent was removed with a rotary evaporator
6. 6
   Sonstigeto give a colorless solid
7. 7
   SonstigeThe solvent was removed with a rotary evaporator
8. 8
   Sonstigethe product was further dried in a vacuum oven at room temperature
9. 9
   Sonstigeto afford 36.4 g of a yellow waxy solid

Vorschrift

A round bottom flask was charged with 1-naphthalenesulfonyl chloride (20.0 g), Na2SO3 (33.36 g), NaHCO3 (22.24 g) and deionized water (350 mL). The mixture was stirred and heated to 65° C. under a nitrogen atmosphere for 2 hours, after which time the mixture was allowed to cool to room temperature and was then further cooled in a refrigerator. The cold mixture was acidified with concentrated H2SO4 which resulted in the formation of a precipitate. The mixture was extracted three times with 100 mL of ethyl acetate. The organic extracts were combined and the solvent was removed with a rotary evaporator to give a colorless solid that was then dissolved in 240 mL of 1:1 (v/v) methanol-deionized water in a beaker. The solution was titrated with a solution of 40% aqueous tetrabutylammonium hydroxide until the pH of the solution was 7.2. The solvent was removed with a rotary evaporator and the product was further dried in a vacuum oven at room temperature to afford 36.4 g of a yellow waxy solid.

Quelle