Glycolic Acid → HCID 15098089, compound

HRID 1384411Notes

Reaction equation

HRID 1384411 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].[CH2:6](Br)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].C(N(CC)CC)C>C(OCC)(=O)C>[O:8]=[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][O:4][C:1](=[O:5])[CH2:2][OH:3]

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 6259Phenacyl bromideHCID 8471Triethylamine

Product 1

HCID 15098089HCID 15098089, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7.61 g of glycolic acid, 19.90 g of phenacylbromide and 13.9 ml of triethylamine in 300 ml of ethyl acetate was stirred for 20 hours at room temperature. Then, the mixture was filtered. The filtrate was washed with 2N HCl, saturated sodium bicarbonate, and brine. Then, the filtrate was dried, filtered again, and evaporated to dryness. The resulting white solid was purified by recrystallization to yield 11.85 g of colorless crystals.

Workup

  1. filtrationThen, the mixture was filtered
  2. washThe filtrate was washed with 2N HCl, saturated sodium bicarbonate, and brine
  3. customThen, the filtrate was dried
  4. filtrationfiltered again
  5. customevaporated to dryness
  6. customThe resulting white solid was purified by recrystallization

Sources & evidence

ORD record
ord-47fa19250a674679b107fcf2099ae598
Source dataset
uspto-grants-2001_07
Patent number
US06258854B1

Reaction notes

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