Ethylene Glycol → HCID 22622966, compound

HRID 840373Notes

Reaction equation

HRID 840373 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13](O)[CH2:14][OH:15].O>C1(C)C=CC=CC=1>[CH2:14]1[O:15][CH:6]([C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=2)[O:7][CH2:13]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 181694-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 22622966HCID 22622966, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25 g of 4-hydroxy-3-nitrobenzaldehyde is mixed in toluene with 1.1 equivalents of ethylene glycol and 370 mg of paratoluenesulfonic acid. It is boiled for 4 hours in a water separator. The mixture is poured onto sodium bicarbonate solution, extracted with ethyl acetate, the organic phase is washed with brine, dried with magnesium sulfate and concentrated by evaporation. 23.6 g of crude product, which is suitable for further reactions, results.

Workup

  1. additionThe mixture is poured onto sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customresults

Sources & evidence

ORD record
ord-c323278b0a674430ab3bdd0558379e4d
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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