Ethylene Glycol → HCID 10889184, compound

HRID 1820604Notes

Reaction equation

HRID 1820604 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:13](O)[CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[O:5]1[CH2:13][CH2:14][O:15][CH:4]1[C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[OH:1]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 668085-NitrosalicylaldehydeHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 10889184HCID 10889184, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The solution of 25 g (149.6 mmol) of 2-hydroxy-5-nitrobenzaldehyde in 500 ml of toluene is mixed with 100 ml of ethylene glycol, 2.85 g of p-toluenesulfonic acid monohydrate, and it is refluxed in a water separator for 5 hours. After cooling, it is poured into saturated sodium bicarbonate solution, extracted several times with ethyl acetate, the combined organic extracts are washed with saturated sodium chloride solution and dried on sodium sulfate. The residue that is obtained after filtration and removal of the solvent is further reacted without being purified.

Workup

  1. temperatureAfter cooling
  2. extractionextracted several times with ethyl acetate
  3. washthe combined organic extracts are washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. customThe residue that is obtained
  6. filtrationafter filtration and removal of the solvent
  7. customis further reacted
  8. customwithout being purified

Sources & evidence

ORD record
ord-9944285d2b944c80ab384c995a45e79c
Source dataset
uspto-grants-2009_10
Patent number
US07605136B2

Reaction notes

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