Iodoethane → Ethyl ester of lactic acid glycolic acid

HRID 234083

Reaction equation

HRID 234083 reaction equation
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:7]([OH:11])(=[O:10])[CH2:8][OH:9].C(I)C.C(=O)([O-])[O-].[K+].[K+]>CC(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

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 36797Hydroxyacetic acid--2-hydroxypropanoic acid (1/1)2×

Product 1

HCID 131719795Ethyl ester of lactic acid glycolic acidYield 142.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

15 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.) and a 7.8 g of ethyl iodide were dissolved in 150 ml of acetone. To thus obtained solution was added 1.38 g of potassium carbonate and then the resulting mixture was refluxed for 6 hours. After the resultant solution was cooled, inorganic substances were removed by filtration and then the filtrate was concentrated under reduced pressure. The concentrate was dissolved in 100 ml of dichloromethane, washed 3 times with 100 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 12.5 g of the ethyl ester of lactic acid/glycolic acid copolymer.

Workup

  1. temperaturethe resulting mixture was refluxed for 6 hours
  2. custominorganic substances were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe concentrate was dissolved in 100 ml of dichloromethane
  5. washwashed 3 times with 100 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

Sources & evidence

ORD record
ord-195799f671a54471a91f42d73a158eeb
Source dataset
uspto-grants-1997_01
Patent number
US05594091

Linked notes

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