Ethylene Glycol → 1,3-Dioxolane, 2-(3-bromo-4-methylphenyl)-

HRID 584313

Reaction equation

HRID 584313 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=[O:6].[CH2:11](O)[CH2:12][OH:13].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:13][CH2:12][CH2:11][O:6]2)[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 8167653-Bromo-4-methylbenzaldehyde

Product 1

HCID 112419791,3-Dioxolane, 2-(3-bromo-4-methylphenyl)-Yield 89.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

11.8 g (60 mmol) of 3-bromo-4-methylbenzaldehyde are placed in 150 ml of toluene in a round-bottomed flask and under nitrogen. 16.5 ml (300 mmol) of ethylene glycol and 571 mg (3 mmol) of para-toluenesulfonic acid are added. The mixture is refluxed for 36 hours and the water formed is separated out using Dean-Stark apparatus. At room temperature, the reaction medium is poured into saturated aqueous sodium hydrogen carbonate solution and then extracted with ether. The organic phase is dried over magnesium sulfate, filtered and evaporated. 13 g (89%) of the expected product are obtained in the form of a brown oil.

Workup

  1. temperatureThe mixture is refluxed for 36 hours
  2. customis separated out
  3. additionAt room temperature, the reaction medium is poured into saturated aqueous sodium hydrogen carbonate solution
  4. extractionextracted with ether
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-282184698f1f435fb04d2ef09b18096f
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Linked notes

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