Reaktion #334274

Reaktionsgleichung

3-nitrobenzaldehyde

1-methyl-2-chloroethyl acetoacetate

hydrogen chloride

→

title compound

Ausbeute 82.9%

1-methyl-2-chloroethyl α-acetyl-3-nitrocinnamate

Ausbeute 82.9%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintained at 0°-5° C.
2. 2
   Sonstigethe residual hydrogen chloride was removed
3. 3
   Sonstigeby bubbling nitrogen through the solution
4. 4
   SonstigeThe toluene was then evaporated off in vacuo
5. 5
   workup.DISSOLUTIONThe residual oil was dissolved in dichloromethane
6. 6
   Sonstigethe solution thus obtained
7. 7
   Waschenwas washed with water until it
8. 8
   SonstigeThe organic phase which was separated
9. 9
   Sonstigedried
10. 10
    Sonstigewas then evaporated to dryness under vacuum at 20° C
11. 11
    SonstigeThe residue was crystallized from 200 ml of isopropanol

Vorschrift

A solution containing 12.2 g of 3-nitrobenzaldehyde and 14.3 g of 1-methyl-2-chloroethyl acetoacetate in 80 ml of toluene, maintained at 0°-5° C., was saturated with hydrogen chloride gas. After two days at 20°-25° C., the residual hydrogen chloride was removed by bubbling nitrogen through the solution. The toluene was then evaporated off in vacuo. The residual oil was dissolved in dichloromethane and the solution thus obtained was washed with water until it was neutral. The organic phase which was separated and dried, was then evaporated to dryness under vacuum at 20° C. The residue was crystallized from 200 ml of isopropanol to give 20.70 g of the title compound, melting at 95°-96° C.

Quelle