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

HRID 10118

Reaktionsgleichung

Reaktionsgleichung von HRID 10118
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14797Potassium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dfe4ced729254e01be55cc9bea0175d5
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094358B2

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