Reaktion #521981

Reaktionsgleichung

sodium hydroxide

methanesulfonic acid

4-dimethylaminobenzaldehyde

3-dimethylaminobenzoic acid

N,N-dimethylaniline

→

2-[bis(4-dimethylaminophenyl)methyl]-5-dimethylaminobenzoic acid

Ausbeute 51.3%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas maintained
2. 2
   Temperaturat reflux temperature
3. 3
   TemperaturAfter cooling
4. 4
   workup.ADDITIONthe resulting solution was added slowly
5. 5
   workup.ADDITIONTwo grams of diatomateous earth was added to the solution
6. 6
   Filtrationthe resulting mixture was clarified by filtration
7. 7
   workup.ADDITIONThe hot filtrate was added slowly
8. 8
   workup.STIRRINGwith stirring to a solution of 100.0 ml of water and 10.0 ml of glacial acetic acid
9. 9
   workup.ADDITIONGlacial acetic acid was added slowly
10. 10
    workup.STIRRINGstirring
11. 11
    workup.WAITwas continued for approximately fifteen minutes
12. 12
    SonstigeThe solid which formed
13. 13
    Filtrationwas collected by filtration
14. 14
    Waschenwashed with water
15. 15
    Sonstigedried at approximately 50° C. in vacuo

Vorschrift

A mixture of 46.0 ml of water, 49.4 g of 70 percent methanesulfonic acid, 14.9 g (0.1 mole) of 4-dimethylaminobenzaldehyde, 16.5 g (0.1 mole) of 3-dimethylaminobenzoic acid and 12.1 g (0.1 mole) of N,N-dimethylaniline was maintained at reflux temperature with stirring for approximately twenty-four hours. After cooling, the resulting solution was added slowly with stirring to a mixture of 700.0 ml of water and 27.0 ml of 50 percent aqueous sodium hydroxide. The resulting solution having a pH of 12.6 was maintained at 60° C. for approximately one hour. Two grams of diatomateous earth was added to the solution and the resulting mixture was clarified by filtration. The hot filtrate was added slowly with stirring to a solution of 100.0 ml of water and 10.0 ml of glacial acetic acid. Glacial acetic acid was added slowly to adjust the pH to 4.9 and stirring was continued for approximately fifteen minutes. The solid which formed was collected by filtration, washed with water and dried at approximately 50° C. in vacuo to obtain 21.4 g of 2-[bis(4-dimethylaminophenyl)methyl]-5-dimethylaminobenzoic acid (Formula II: Y=4-N(CH3)2 ; R=R1 =R2 =R3 =CH3), a pale green-colored solid which melted over the range of 179° to 184° C. After one recrystallization from toluene, the melting point was 210° to 212° C.

Quelle