Reacción #64047

Ecuación de reacción

3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)-2-butyrylcyclohex-2-en-1-one

sodium hydroxide

Sodium dithionite

→

3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)-2-butyrylcyclohex-2-en-1-one

Rendimiento 32.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaunder reflux
3. 3
   Temperaturarefluxing
4. 4
   FiltraciónThe reaction mixture was filtered while still hot and the filtrate
5. 5
   workup.ADDITIONwas diluted with water (100 ml)
6. 6
   Extracciónfinally extracted with dichloromethane (2×100 ml)
7. 7
   OtroEvaporation of the dichloromethane layer

Procedimiento

A solution of 3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)-2-butyrylcyclohex-2-en-1-one (3.3 g, 0.01 mole) and sodium hydroxide (38 g) in 50% aqueous ethanol (120 ml) was stirred and heated under reflux. Sodium dithionite (9.6 g, 0.05 mole) was added in portions over a period of 30 minutes to the solution and refluxing was continued for 1 hour. The reaction mixture was filtered while still hot and the filtrate was diluted with water (100 ml), neutralized with hydrochloric acid and finally extracted with dichloromethane (2×100 ml). Evaporation of the dichloromethane layer gave 3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)-2-butyrylcyclohex-2-en-1-one (0.96 g, 32%) as an orange oil. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm); 1.00 (3H, t); 1.5 (2H, m); 2.14 (3H, s); 2.22 (3H, s); 2.30 (3H, s); 2.4-4.0 (7H, m); 6.78 (1H, s); exchangeable protons not observed.

Fuente