Chloroacetic Acid → BnO-PEG5-CH2COOH

HRID 1162953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162953
N[C@H](C=O)CCSC.[CH2:9]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[CH2:33][C:34]([OH:36])=[O:35]>O>[CH2:9]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:33][C:34]([OH:36])=[O:35])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 300Chloroacetic AcidHCID 446793Methionin ALHCID 135536921-Phenyl-2,5,8,11,14-pentaoxahexadecan-16-ol

Produkt 1

HCID 57557922BnO-PEG5-CH2COOHAusbeute 201,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Metal sodium (115 mg, 5.0 mmol) was added to pentaethylene glycol monobenzyl ether (328 mg, 1.0 mmol), and the mixture was stirred at 90° C. for three hours. Chloroacetic acid (47 mg, 0.5 mmol) was added to the mixture which was then stirred at 90° C. for 16 hours. Water was added to the mixture which was then washed with ethyl acetate. Next, the aqueous layer was made acidic by 1 N hydrochloric acid, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain 390 mg of crude [2-(2-{2-[2-(2-benzyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid in the form of a reddish brown substance.

Aufarbeitung

  1. stirringwas then stirred at 90° C. for 16 hours
  2. washwas then washed with ethyl acetate
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c73672c523748d49daad8324589ac51
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820693B2

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