Réaction #10214

Équation de réaction

4-hydroxybenzoic acid

6-chloro-1-hexanol

→

4-(6-hydroxyhexyloxy)-benzoic acid

Rendement 80.0%

Solvants

KOH

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source