Reacción #93501

Ecuación de reacción

acetic acid, 4-[4-(acetylamino)phenyl]butyl ester

potassium carbonate

→

title compound

4-(Acetylamino)benzenebutanol

Disolventes

ethanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide, 90:10)
2. 2
   OtroAt the completion of the reaction
3. 3
   Filtraciónfilter off any insolubles
4. 4
   Otroremove the ethanol in vacuo
5. 5
   ExtracciónExtract the aqueous residue with 3×300 ml methylene chloride
6. 6
   LavadoWash the combined organic layers with 100 ml water
7. 7
   Secadodry over potassium carbonate
8. 8
   Filtraciónfilter
9. 9
   Otroremove the solvent in vacuo
10. 10
    OtroRecrystallize the resulting solid from 140 ml acetonitrile

Procedimiento

To a solution of 19.3 g (0.077 mole) of acetic acid, 4-[4-(acetylamino)phenyl]butyl ester in 300 ml of ethanol, add a solution of 21 g potassium carbonate in 300 ml of water. Heat the resulting solution at 55° C. for 4 hrs, following the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile: ammonium hydroxide, 90:10). At the completion of the reaction, filter off any insolubles and remove the ethanol in vacuo. Extract the aqueous residue with 3×300 ml methylene chloride. Wash the combined organic layers with 100 ml water, dry over potassium carbonate, filter and remove the solvent in vacuo. Recrystallize the resulting solid from 140 ml acetonitrile to obtain the title compound.

Fuente