Ethylene Glycol → HCID 15672401, compound

HRID 1494550Notes

Reaction equation

HRID 1494550 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:17][C:18]1[N:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[C:21]([C:28]([O:30][CH3:31])=[O:29])=[CH:20][C:19]=1[CH:32]=O.C1(C)C=CC=CC=1>CCOCC>[Cl:17][C:18]1[N:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[C:21]([C:28]([O:30][CH3:31])=[O:29])=[CH:20][C:19]=1[CH:32]1[O:4][CH2:1][CH2:2][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 15672398HCID 15672398, compound

Product 1

HCID 15672401HCID 15672401, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethylene glycol (14.3 mL, 0.255 mol), and a catalytic amount of p-toluenesulfonic acid monohydrate is added to a solution of 6-chloro-5-formyl-2,3-pyridinedicarboxylic acid, dimethyl ester, 5-(dimethyl acetal) (15.46 g, 0.051 mol) and toluene. The reaction mixture is heated at reflux temperature for 3 hours then cooled to room temperature. Ether is added and the mixture is washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound as an orange oil (14.27 g, 93%), identified by IR and NMR spectral analyses.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature for 3 hours
  3. washthe mixture is washed with saturated sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d9c92df261a475fbb1320f39b0eddef
Source dataset
uspto-grants-1991_06
Patent number
US05026859

Reaction notes

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