Ethanol → Ethyl ester of lactic acid glycolic acid
Reaction equation
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:7]([OH:11])(=[O:10])[CH2:8][OH:9].ClCCl.C(O)C>O>[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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
6 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 60 ml of dichloromethane and 60 ml of ethanol. While thus obtained solution was cooled and stirred, 3.83 g of 1-ethyl-3-(3-dimethylaminoisopropyl)-carbodiimide hydrochloride was added and then the reaction mixture was stirred overnight. After 50 ml of water was added, dichloromethane phase was separated. The dichloromethane phase was washed 2 times with 40 ml of 10% ethanol-water and dried with magnesium sulfate. After magnesium sulfate was separated by filtration, the mixture was concentrated to dryness under reduced pressure to yield 5.2 g of the ethyl ester of lactic acid/glycolic acid copolymer.
Workup
- dissolutionwas dissolved in a mixed solvent
- temperatureWhile thus obtained solution was cooled
- stirringthe reaction mixture was stirred overnight
- customdichloromethane phase was separated
- washThe dichloromethane phase was washed 2 times with 40 ml of 10% ethanol-water
- dry with materialdried with magnesium sulfate
- customAfter magnesium sulfate was separated by filtration
- concentrationthe mixture was concentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-798abe379f8141c791fb77e5632279c1
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665394
Reaction notes
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