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

HRID 1769196Notes

Reaction equation

HRID 1769196 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].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=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

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 707414-Bromobenzaldehyde

Product 1

HCID 27738422-(4-Bromophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 100 g 4-bromobenzaldehyde, 40 ml ethylene glycol, 800 ml of toluene and a catalytic amount of p-toluenesulfonic acid was refluxed for 2 hours, removing water with a Dean-Stark trap. The mixture was then cooled and poured into cold dilute potassium carbonate solution, extracted three times with ether and dried (MgSO4). Solvent was removed under reduced pressure, giving 118 g of 4-bromobenzaldehyde ethylene ketal (23) as a solid.

Workup

  1. customremoving water with a Dean-Stark trap
  2. temperatureThe mixture was then cooled
  3. additionpoured into cold dilute potassium carbonate solution
  4. extractionextracted three times with ether
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-66818a250b3a4f4494d532220960e1d8
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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