Benzene → 2-(Bromomethyl)-2,4-bis(4-chlorophenyl)-1,3-dioxolane

HRID 1390588Notes

Reaction equation

HRID 1390588 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:22])[CH2:20]O)=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[O:22][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)[CH2:20][O:4]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 68303p-Chlorophenacyl bromideHCID 1011071-(4-Chlorophenyl)-1,2-ethanediol

Product 1

HCID 203326202-(Bromomethyl)-2,4-bis(4-chlorophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

a mixture of 11.7 parts of 2-bromo-4'-chloroacetophenone, 9 parts of 1-(p-chlorophenyl)-1,2-ethanediol, 0.5 parts of p-toluenesulfonic acid and 80 parts of benzene is stirred and refluxed for 2 days with water-separator. The reaction mixture is cooled and washed successively twice with a sodium hydrogen carbonate solution and once with water. The organic phase is dried and evaporated. The residue is triturated in petroleum ether and cooled on ice. The precipitated product is filtered off, crystallized from methanol, stirred in acetonitrile while cooling on ice, filtered off again and washed once more with acetonitrile, yielding 2-(bromomethyl)-2,4-bis(p-chlorophenyl)-1,3-dioxolane.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washwashed successively twice with a sodium hydrogen carbonate solution and once with water
  3. customThe organic phase is dried
  4. customevaporated
  5. customThe residue is triturated in petroleum ether
  6. temperaturecooled on ice
  7. filtrationThe precipitated product is filtered off
  8. customcrystallized from methanol
  9. stirringstirred in acetonitrile
  10. temperaturewhile cooling on ice
  11. filtrationfiltered off again
  12. washwashed once more with acetonitrile

Sources & evidence

ORD record
ord-c4db3aea653b469e866ac49da0c0f32f
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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