Hydrochloric Acid → 8-phenoxyoctanoic Acid

HRID 377471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377471
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].Cl>CCO.O>[O:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 14798Sodium HydroxideHCID 5482758-Bromooctanoic acid

Produkt 1

HCID 102203288-phenoxyoctanoic AcidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Phenol (1.88 g, 20 mmol) was mixed with NaOH (0.80 g, 20 mmol) in EtOH (50 mL). 8-Bromooctanoic acid (2.23 g, 10 mmol) was then added to the mixture and refluxed for 12 h. After cooling to room temperature, water (100 mL) was added and the mixture was acidified with 2N HCl (pH=2). The solid was filtered and washed with water (2×50 mL), and recrystallized from hexane-ethyl acetate (5:1) to give the product as white brick-like crystals (1.79 g, 76%), mp 67-68° C.; 1H-NMR: 1.42 (m, 6H), 1.65 (m, 2H), 1.80 (m, 2H), 2.37 (t, 2H), 3.97 (t, 2H), 6.93 (m, 3H), 7.30 (t, 2H), 10.05 (bs, 1H). Anal. Calcd. for C14H20O3 : C, 71.16, H, 8.53%; Found: C, 71.09, H, 8.54%.

Aufarbeitung

  1. temperaturerefluxed for 12 h
  2. filtrationThe solid was filtered
  3. washwashed with water (2×50 mL)
  4. customrecrystallized from hexane-ethyl acetate (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-26a508be8fb041a2bd658dae9592574d
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025511

Notizen zur Reaktion

Wird geladen…