Reacción #63561

Ecuación de reacción

benzyl bromide

sodium hydroxide

5-hydroxy-2-methoxybenzaldehyde

→

5-benzyloxy-2-methoxybenzaldehyde

Rendimiento 91.0%

Disolventes

dichloromethane

water

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared by the method of Ulrich et al, J.Org.Chem
2. 2
   TemperaturaThe mixture became warm
3. 3
   workup.DISSOLUTIONthe suspension dissolved
4. 4
   Otrocrystallisation of the benzylated product
5. 5
   Otrothe organic layer was removed
6. 6
   Lavadowashed twice with water, once with saturated sodium chloride solution
7. 7
   Secadodried with anhydrous magnesium sulphate
8. 8
   ConcentraciónThe solution was concentrated
9. 9
   workup.ADDITIONtreated with petroleum spirit

Procedimiento

To a stirred suspension of 5-hydroxy-2-methoxybenzaldehyde (306.6 g, prepared by the method of Ulrich et al, J.Org.Chem., 1974, 39, 2437), benzyl bromide (355.8 g) and Adogen 464 (48.5 g) in dichloromethane (600 ml) was added a solution of sodium hydroxide (123.5 g) in water (500 ml). The mixture became warm and the suspension dissolved; additional dichloromethane (300 ml) was added to prevent crystallisation of the benzylated product. After 2 hours, the organic layer was removed, washed twice with water, once with saturated sodium chloride solution, then dried with anhydrous magnesium sulphate. The solution was concentrated, then treated with petroleum spirit to give 5-benzyloxy-2-methoxybenzaldehyde (445.7 g, 91%), m.p. 99°-100°.

Fuente