Bromoacetate → 2-(2-(Benzyloxy)ethoxy)acetic acid

HRID 278528

Reaktionsgleichung

Reaktionsgleichung von HRID 278528
Br[CH2:2][C:3]([O-:5])=[O:4].[CH2:6]([O:13][CH:14]([O-])[CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH:17]S([O-])(=O)=O.[K+]>C(OCC)(=O)C>[C:7]1([CH2:6][O:13][CH2:14][CH2:15][O:17][CH2:2][C:3]([OH:5])=[O:4])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 6226BromoacetateHCID 516920Potassium bisulfateHCID 22628633Benzyloxyethanolate

Produkt 1

HCID 217901362-(2-(Benzyloxy)ethoxy)acetic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

This solution of bromoacetate is added dropwise to the prepared solution of benzyloxyethanolate anion, and the mixture is heated at reflux for 19 h. The reaction is stopped with 5% KHSO4. 250 ml ethyl acetate is added and the organic phase is extracted three times with the aid of 5% NaOH. The pH of the alkaline phase is reduced to 1 with 10% HCl and extraction is performed twice with EtOAc. The organic phase is washed three times with sodium chloride solution, dried on Na2SO4, and evaporated to obtain 6.4 g (93%) 7-phenyl-3,6-dioxaheptanoic acid in the form of a colourless liquid.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 19 h
  3. extractionthe organic phase is extracted three times with the aid of 5% NaOH
  4. extractionThe pH of the alkaline phase is reduced to 1 with 10% HCl and extraction
  5. washThe organic phase is washed three times with sodium chloride solution
  6. customdried on Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c24808a6ee6248c4ba1399538a1d3c69
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359168B1

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