Ethylene Glycol → 2-(4-Bromophenyl)-1,3-dioxolane

HRID 439812Notes

Reaction equation

HRID 439812 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.O>C1C=CC=CC=1>[CH2:11]1[O:12][CH:6]([C:5]2[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=2)[O:7][CH2:10]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 707414-Bromobenzaldehyde

Product 1

HCID 27738422-(4-Bromophenyl)-1,3-dioxolaneYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-bromobenzaldehyde (102 g, 0.55 mol) and ethylene glycol (100 g, 1.65 mol) in benzene (1 l) were added a small amount of 10-camphorsulfonic acid, and the mixture was refluxed for 3 hours, while water was removed with Dean-Stark. After allowing to cool, saturated sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled to give the title compound (126 g, 0.55 mol, 100%).

Workup

  1. customwas removed with Dean-Stark
  2. temperatureto cool
  3. additionsaturated sodium hydrogencarbonate solution was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled

Sources & evidence

ORD record
ord-c3100e4ab8a74764a1978c3a4774c7b1
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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