Ethanol → Ethyl ester of lactic acid glycolic acid

HRID 234084

Reaktionsgleichung

Reaktionsgleichung von HRID 234084
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:7]([OH:11])(=[O:10])[CH2:8][OH:9].C(O)C.ClC(OCC)=O>O.ClCCl.C(N(CC)CC)C>[CH3:7][CH2:8][O:5][C:1]([CH:2]([OH:3])[CH3:4])=[O:6].[C:7]([OH:11])(=[O:10])[CH2:8][OH:9]

Komponenten

7

Edukt 3

HCID 702EthanolHCID 10928Ethyl chloroformateHCID 36797Hydroxyacetic acid--2-hydroxypropanoic acid (1/1)2×

Produkt 1

HCID 131719795Ethyl ester of lactic acid glycolic acidAusbeute 146,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

9 g of a lactic acid/glycolic acid copolymer having a weight-average molecular weight of about 7,500 (lactic acid/glycolic acid=75/25 (mol %)) (Wako Pure Chemical Industries, Ltd.) was dissolved in a mixed solvent consisting of 20 ml of dichloromethane and 20 ml of ethanol. While thus obtained solution was cooled and stirred, 0.45 ml of triethyl amine, 0.29 ml of ethyl chloroformate and 0.36 g of N,N-dimethylaminopyridine were added. After the resulting mixture was stirred for another 2 hours, 50 ml of dichloromethane and 50 ml of water were added and then dichloromethane phase was separated. The dichloromethane phase was washed 2 times with 50 ml of 10% ethanol-water, and then dried with magnesium sulfate. After magnesium sulfate was separated by filtration, the mixture was concentrated to dryness under reduced pressure to yield 7.7 g of the ethyl ester of lactic acid/glycolic acid copolymer.

Aufarbeitung

  1. dissolutionwas dissolved in a mixed solvent
  2. temperatureWhile thus obtained solution was cooled
  3. stirringAfter the resulting mixture was stirred for another 2 hours
  4. customdichloromethane phase was separated
  5. washThe dichloromethane phase was washed 2 times with 50 ml of 10% ethanol-water
  6. dry with materialdried with magnesium sulfate
  7. customAfter magnesium sulfate was separated by filtration
  8. concentrationthe mixture was concentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-38b6023ee63b4506908dd3ebfbe2100e
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594091

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