4-Hydroxybenzoic Acid → 4-(Octyloxy)benzoic acid

HRID 247798

Reaktionsgleichung

Reaktionsgleichung von HRID 247798
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O.C(OCC)C>[CH2:1]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

8

Edukt 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric Acid2×HCID 81401-BromooctaneHCID 11430Potassium Carbonate

Produkt 1

HCID 172314-(Octyloxy)benzoic acidAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of octylbromide (4.19 g), 4-hydroxybenzoic acid (3 g) and potassium carbonate (3 g) in dimethylformamide (100 ml) was stirred at 130° C. for two hours. The solution was poured in water and neutralized with dilute aqueous hydrochloric acid solution. Diethylether was added to effect extraction. After the extracted layer was distilled to remove the solvent, the residue was added to a solution of sodium hydroxide (3.3 g), water (10 ml) and ethanol (50 ml). The solution obtained was refluxed for about a day and neutralized with dilute aqueous hydrochloric acid solution. The solution was distilled to remove the solvent and concentrated. The solid obtained was collected and recrystallized from water/ethanol to obtain the titled compound (3.88 g).

Aufarbeitung

  1. distillationAfter the extracted layer was distilled
  2. customto remove the solvent
  3. additionthe residue was added to a solution of sodium hydroxide (3.3 g), water (10 ml) and ethanol (50 ml)
  4. customThe solution obtained
  5. distillationThe solution was distilled
  6. customto remove the solvent
  7. concentrationconcentrated
  8. customThe solid obtained
  9. customwas collected
  10. customrecrystallized from water/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4ec4327d040a4a578173b0f6893bc343
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05207947

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