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

HRID 1249955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1249955
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].[I-].[K+].Cl>CO.O>[OH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 748286-Chloro-1-hexanol

Produkt 1

HCID 36284134-(6-Hydroxyhexyloxy)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

229.2 g (1.66 mol) of p-hydroxy-benzoic acid were dissolved in 600 ml of methanol and treated at 0° C. within 10 minutes with a solution of 151 g (3.77 mol) of NaOH in 480 ml of H2O. 271.2 g (1.99 mol) of 6-chloro-hexanol were slowly added dropwise to this solution. Finally, 0.75 g of potassium iodide was added and the batch was boiled under reflux for 60 hours. For the working up, the yellow solution was poured into 3 1 of H2O and treated with 10% HCl (about 600 ml) until a pH value of 1 had been achieved. The milky suspension was filtered over a large suction filter. The residue was sucked dry and recrystallized twice from about 1.5 l of ethanol. This gave 229.6 g of 4-(6-hydroxy-hexyloxy)-benzoic acid as a fine white powder; m.p. 136-141° C.

Aufarbeitung

  1. temperatureunder reflux for 60 hours
  2. filtrationThe milky suspension was filtered over a large suction
  3. filtrationfilter
  4. customThe residue was sucked dry
  5. customrecrystallized twice from about 1.5 l of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-65c244dffd414df49b550b177c4c863c
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06335409B1

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