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

HRID 1654738Notes

Reaction equation

HRID 1654738 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 (1l) 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-f1e6728c635e4a4882d9b5704fb1a653
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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