Reacción #10214

Ecuación de reacción

4-hydroxybenzoic acid

6-chloro-1-hexanol

→

4-(6-hydroxyhexyloxy)-benzoic acid

Rendimiento 80.0%

Disolventes

KOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAbout 1% of KI was added as a catalyst
2. 2
   TemperaturaAfter refluxing the reaction mixture for extended period of time (2-15 hrs) the contents
3. 3
   Temperaturawas cooled
4. 4
   Filtraciónthe reaction mixture was filtered off
5. 5
   Otrothe filtrate solvent was evaporated under vacuum
6. 6
   workup.ADDITIONWater was added into the residue
7. 7
   Filtraciónthe precipitate was filtered
8. 8
   Otrocrystallized with ethanol

Procedimiento

Monomers in which the bulky organic group was a t-butyl group and the alkyl groups were hexyl groups were made as follows. 4-hydroxybenzoic acid was dissolved in 30% ethanolic KOH. About 1% of KI was added as a catalyst. The mixture was heated to about 60° C. and a stoichiometric amount of 6-chloro-1-hexanol was slowly added over about ½ hour. After refluxing the reaction mixture for extended period of time (2-15 hrs) the contents was cooled, the reaction mixture was filtered off, and the filtrate solvent was evaporated under vacuum. Water was added into the residue and acidified with HCl and the precipitate was filtered and crystallized with ethanol, yielding approximately an 80% 4-(6-hydroxyhexyloxy)-benzoic acid.

Fuente