Reaktion #63828

Reaktionsgleichung

hydrochloric acid

1-chloro-2-methoxy-4-nitrobenzene

sodium hydroxide

4-chlorobenzeneacetonitrile

→

α-(4-chlorophenyl)-2-methoxy-4-nitrobenzeneacetonitrile

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added dropwise, during a 5 minutes period
2. 2
   workup.ADDITIONThe reaction mixture is poured into 2000 parts of crushed ice
3. 3
   SonstigeThe layers are separated
4. 4
   ExtraktionThe aqueous phase is extracted with dichloromethane
5. 5
   SonstigeThe combined extracts are dried
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue is crystallized from 2,2'-oxybispropane
9. 9
   FiltrationThe product is filtered off
10. 10
    Sonstigedried

Vorschrift

To a stirred mixture of 68 parts of 1-chloro-2-methoxy-4-nitrobenzene, 230 parts of a sodium hydroxide solution 50%, 5 parts of N,N,N-triethylbenzenemethanaminium chloride and 360 parts of tetrahydrofuran is added dropwise, during a 5 minutes period, a solution of 43.2 parts of 4-chlorobenzeneacetonitrile in 90 parts of tetrahydrofuran. Upon completion, stirring is continued for 4 hours at 60° C. The reaction mixture is poured into 2000 parts of crushed ice. The whole is acidified with concentrated hydrochloric acid. The layers are separated. The aqueous phase is extracted with dichloromethane. The combined extracts are dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding α-(4-chlorophenyl)-2-methoxy-4-nitrobenzeneacetonitrile.

Quelle