Reacción #65902

Ecuación de reacción

methyl-t-butyl ether

sodium cyanide

sodium bisulfite

p-anisaldehyde

→

p-methoxybenzaldehyde cyanohydrin

Disolventes

water

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe slurry is cooled to 5° C.
2. 2
   workup.STIRRINGThe reaction is stirred for 2 hrs
3. 3
   Temperaturaat 5° C., then warmed to room temperature
4. 4
   OtroThe layers are separated after a brief stir
5. 5
   Extracciónthe aqueous phase re-extracted with MTBE (100 ml)
6. 6
   SecadoThe combined organic layers were dried (MgSO4)
7. 7
   Concentraciónconcentrated to an oil, which
8. 8
   Otroto afford product
9. 9
   OtroThe material can be recrystallized from toluene (3 ml per g substrate, heat to 35° C., cool to 5° C., 90% recovery)

Procedimiento

Water (720 ml), sodium bisulfite (81 g, 0.775 mol, 1.2 equiv) and p-anisaldehyde (88 g, 0.646 mol, 1.0 equiv) are combined, warmed to 40° C. and stirred for 3 hrs. The slurry is cooled to 5° C., and sodium cyanide (35 g, 0.711 mol, 1.1 equiv) in 140 ml water is added. The reaction is stirred for 2 hrs. at 5° C., then warmed to room temperature, and methyl-t-butyl ether (MTBE) (400 ml) added. The layers are separated after a brief stir, and the aqueous phase re-extracted with MTBE (100 ml). The combined organic layers were dried (MgSO4), and concentrated to an oil, which was seeded to afford product: 69.5 g, 65.9%. The material can be recrystallized from toluene (3 ml per g substrate, heat to 35° C., cool to 5° C., 90% recovery).

Fuente