Chloroacetic Acid → 2-(2-Phenylethoxy)acetic acid

HRID 2100466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2100466
[H-].[Na+].[C:3]1([CH2:9][CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:13][C:14]([OH:16])=[O:15]>CN(C=O)C>[CH2:10]([O:11][CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 300Chloroacetic AcidHCID 60542-PhenylethanolHCID 24758Sodium hydride

Produkt 1

HCID 132089222-(2-Phenylethoxy)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (6.87 g, 172 mmol) was added slowly to a solution of 2-phenylethanol ([60-12-8], 6.00 g, 5.88 ml, 49.1 mmol) in DMF (50 ml). The reaction mixture was heated and kept for 10 min at 60° C. Chloroacetic acid ([79-11-8], 8.12 g, 86 mmol) was added slowly and carefully (exothermic), and the mixture was kept for 1 h at 60° C. The mixture was poured on ice and extracted twice with diethyl ether. Then the water phase was acidified (HCl, pH˜3) and extracted twice with ethyl acetate. Phenethyloxy-acetic acid [81228-03-7] was obtained after drying (Na2SO4), and evaporation of the solvent. The compound was sufficiently pure for the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. waitcarefully (exothermic), and the mixture was kept for 1 h at 60° C
  3. additionThe mixture was poured on ice
  4. extractionextracted twice with diethyl ether
  5. extractionextracted twice with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c256d2f4d59f47debb4ff954785466ea
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572801B2

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