Hydroxyacetic acid--2-hydroxypropanoic acid (1/1) → Ethyl ester of lactic acid glycolic acid

HRID 234082

Reaction equation

HRID 234082 reaction equation
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:7]([OH:11])(=[O:10])[CH2:8][OH:9].[N+](=CC)=[N-]>ClCCl>[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

4

Reactant 2

HCID 36797Hydroxyacetic acid--2-hydroxypropanoic acid (1/1)2×HCID 70695Diazoethane

Product 1

HCID 131719795Ethyl ester of lactic acid glycolic acidYield 172.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

130 g of lactic acid/glycolic acid copolymer having a weight-average molecular weight of about 5,000, (lactic acid/glycolic acid=50/50 (mol %)) was dissolved in 1,900 ml of dichloromethane; this solution was stirred and cooled. While the solution was ice cooled, the above-described diazoethane solution was added dropwise, followed by stirring at room temperature for 2 hours. After the solution was kept standing overnight, the solvent was distilled off under reduced pressure; the residue was vacuum dried at room temperature to yield 131 g of the ethyl ester of lactic acid/glycolic acid.

Workup

  1. temperaturecooled
  2. temperaturecooled
  3. stirringby stirring at room temperature for 2 hours
  4. distillationthe solvent was distilled off under reduced pressure
  5. customdried at room temperature

Sources & evidence

ORD record
ord-964e102c196d46ae806bc5893ec44bb2
Source dataset
uspto-grants-1997_01
Patent number
US05594091

Linked notes

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