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

HRID 1883205Notes

Reaction equation

HRID 1883205 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[O:12][CH2:11][CH2:10][O:5]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 811292-Bromobenzaldehyde

Product 1

HCID 5535342-(2-Bromophenyl)-1,3-dioxolaneYield 95%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

2-Bromobenzaldehyde (11.4 g) was dissolved in toluene (150 mL), and thereto were added ethyleneglycol (4.58 g) and p-toluenesulfonic acid monohydrate (135 mg), and the mixture was refluxed for 6 hours with azeotropic distillation. The reaction solution was washed with an aqueous sodium hydrogen carbonate solution, and the solvent was evaporated under reduced pressure to give 2-(2-bromophenyl)-1,3-dioxolane (13.4 g, 95%).

Workup

  1. temperaturethe mixture was refluxed for 6 hours with azeotropic distillation
  2. washThe reaction solution was washed with an aqueous sodium hydrogen carbonate solution
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7023fe0bff034beb8993338f6bb7ba2b
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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