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

HRID 329661Notes

Reaction equation

HRID 329661 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(S(O)(=O)=O)=CC=1>C1(C)C=CC=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 3

HCID 174Ethylene Glycol2×HCID 6101p-Toluenesulfonic acidHCID 811292-Bromobenzaldehyde

Product 1

HCID 5535342-(2-Bromophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 50.0 g of 2-bromobenzaldehyde in 50 ml of toluene was added ;b 25.0 ml of ethylene glycol plus 500 mg of p-toluenesulfonic acid. The mixture was heated at reflux with a Dean Stark Trap for 18 hours. Then an additional 10 ml of ethylene glycol was added to the mixture and reflux was continued for 4 hours longer. The solvent was evaporated in vacuo and the residue was dissolved in ether. The organic solution was washed with 5% sodium bicarbonate, dried over magnesium sulfate and filtered. The filtrate was evaporated to an oil which was distilled through a Kugelrohr apparatus. The fraction boiling at 130° C., 0.1 mm was collected giving 60.3 g of 2-(2-bromophenyl)-1,3-dioxolane.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux with a Dean Stark Trap for 18 hours
  3. temperaturereflux
  4. customThe solvent was evaporated in vacuo
  5. dissolutionthe residue was dissolved in ether
  6. washThe organic solution was washed with 5% sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated to an oil which
  10. distillationwas distilled through a Kugelrohr apparatus
  11. customThe fraction boiling at 130° C., 0.1 mm was collected

Sources & evidence

ORD record
ord-1a030d5b528d4095986bddaf671853e3
Source dataset
uspto-grants-1990_01
Patent number
US04892885

Reaction notes

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