Reacción #569999

Ecuación de reacción

hydrochloric acid

active amyl alcohol

pyridine

terephthalaldehydic acid chloride

→

p-(2-methylbutoxycarbonyl)benzaldehyde

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   Temperaturaheated
3. 3
   Temperaturaunder reflux for 2 hours
4. 4
   Temperaturafurther cooled with ice
5. 5
   Otroto remove pyridine in the organic layer
6. 6
   LavadoThe organic layer was then washed successively with water, 2N aqueous sodium hydroxide solution
7. 7
   workup.DISTILLATIONToluene as a solvent was distilled off in vacuum
8. 8
   Otrothe remaining reaction product
9. 9
   workup.DISTILLATIONwas distilled in vacuum

Procedimiento

315 g of said terephthalaldehydic acid chloride dissolved in 400 ml of toluene was dropped into an ice-cooled mixed solution of commercially available S(-)-2-methylbutanol (optically active amyl alcohol) and 230 g of pyridine, and heated under reflux for 2 hours. The reaction solution was cooled to room temperature and further cooled with ice, and acidified by adding 6N hydrochloric acid thereto to remove pyridine in the organic layer. The organic layer was then washed successively with water, 2N aqueous sodium hydroxide solution, and again with water. Toluene as a solvent was distilled off in vacuum, and the remaining reaction product was distilled in vacuum to obtain p-(2-methylbutoxycarbonyl)benzaldehyde (b.p. 118°-124° C./3.5 Torr).

Fuente