4-Hydroxybenzoic Acid → 4-(6-Hydroxyhexyloxy)benzoic acid

HRID 720808Notes

Reaction equation

HRID 720808 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]>[OH-].[K+]>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 748286-Chloro-1-hexanol

Product 1

HCID 36284134-(6-Hydroxyhexyloxy)benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  1. additionAbout 1% of KI was added as a catalyst
  2. temperatureAfter refluxing the reaction mixture for extended period of time (2–15 hrs) the contents
  3. temperaturewas cooled
  4. filtrationthe reaction mixture was filtered off
  5. customthe filtrate solvent was evaporated under vacuum
  6. additionWater was added into the residue
  7. filtrationthe precipitate was filtered
  8. customcrystallized with ethanol

Sources & evidence

ORD record
ord-9d7516dc13234eaa981394c28f059351
Source dataset
uspto-grants-2006_11
Patent number
US07135589B2

Reaction notes

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