Reaktion #1091

Reaktionsgleichung

methanol

2-carboxy-5-nitrobenzenesulfonic acid

thionyl chloride

→

2-methoxycarbonyl-5-nitrobenzenesulfonic acid

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis heated
2. 2
   SonstigeAfter separating off the insoluble constituents
3. 3
   Filtrationby filtration
4. 4
   Einengenthe filtrate is concentrated
5. 5
   Sonstigeresults
6. 6
   workup.ADDITIONWhen addition
7. 7
   SonstigeThe solid which precipitates
8. 8
   Filtrationis filtered off
9. 9
   Sonstigedried

Vorschrift

A suspension of 190.0 g (0.77 mol) of 2-carboxy-5-nitrobenzenesulfonic acid, 10 ml of DMF and 250 ml (3.43 mol) of thionyl chloride is heated at boiling for 3 h. After separating off the insoluble constituents by filtration, the filtrate is concentrated. 200 ml (4.94 mol) of methanol are added to the residue which results. When addition is complete the reaction mixture is cooled to 0° C. The solid which precipitates is filtered off and dried. 70.9 g (35.3% of theory) of colorless, crystalline 2-methoxycarbonyl-5-nitrobenzenesulfonic acid (m.p.: 92°-94° C.) are thus obtained. By distilling off the volatile components from the mother liquor, a second fraction (62.5 g, 31.1% of theory) is obtained.

Quelle