Ethylene Glycol → HCID 22033390, compound

HRID 1792415Notes

Reaction equation

HRID 1792415 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][CH:3]=1.[CH2:10]([OH:13])[CH2:11][OH:12].[C:14]1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:5]=[CH:4][C:3]=1[CH:11]1[CH2:10][O:13][CH2:14][O:12]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 707414-Bromobenzaldehyde

Product 1

HCID 22033390HCID 22033390, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

In a round-bottomed flask equipped with a Dean Stark trap and a condenser, was added a solution of p-Bromobenzaldehyde (5 g, 27 mmol) in toluene (25 mL). To this mixture were then added p-toluenesulfonic acid (50 mg, 0.26 mmol) and etylene glycol (1.84 g, 29.7 mmol). The mixture was heated to reflux under nitrogen atmosphere for 8 h. The progress of the reaction was monitored by TLC. When the reaction was complete, the mixture was cooled down, the solvent was removed under reduced pressure, the residue material was distilled to give an oil (5.49 g, 89%).

Workup

  1. customIn a round-bottomed flask equipped with a Dean Stark trap and a condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux under nitrogen atmosphere for 8 h
  4. temperaturethe mixture was cooled down
  5. customthe solvent was removed under reduced pressure
  6. distillationthe residue material was distilled

Sources & evidence

ORD record
ord-8f46b3be43a246868cb922f99a121180
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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