Glycolic Acid → HCID 18506466, compound

HRID 1585499Notes

Reaction equation

HRID 1585499 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].[CH2:6](I)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C1CCN2C(=NCCC2)CC1>CC#N>[OH:3][CH2:2][C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:4]

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 125271-IodohexaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 18506466HCID 18506466, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 215 mg (2.82 mmol) glycolic acid in 12.8 ml CH3CN was added 719 mg (3.39 mmol) 1-hexyl iodide and 429 mg (2.82 mmol) DBU. After stirring over night and reflux for 4 h, the solvent was evaporated, ethylacetat and 1 M KHSO4 was added and the phases were separated. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give 333 mg (74%) of the product.

Workup

  1. temperaturereflux for 4 h
  2. customthe solvent was evaporated
  3. additionethylacetat and 1 M KHSO4 was added
  4. customthe phases were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-b78ea061c45742f99c4c70ecb39f3dd6
Source dataset
uspto-grants-1999_08
Patent number
US05939392

Reaction notes

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