Ethylene Glycol → 2-(3-Bromo-o-tolyl)-2-methyl-1,3-dioxolane

HRID 258909Notes

Reaction equation

HRID 258909 reaction equation
[Br:1][C:2]1[C:3](C)=[C:4]([C:8](=O)C)[CH:5]=[CH:6][CH:7]=1.[C:12]1(C)C=CC(S(O)(=O)=O)=C[CH:13]=1.[C:23](=[O:26])([O-])[O-:24].[Na+].[Na+].[CH2:29](O)CO>O.C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([C:23]2([CH3:29])[O:26][CH2:13][CH2:12][O:24]2)=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 174Ethylene Glycol2×HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 204801311-(3-Bromo-2-methylphenyl)ethanone

Product 1

HCID 706381482-(3-Bromo-o-tolyl)-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 100 parts of 3'-bromo-2'-methylacetophenone, 30 parts of ethylene glycol, 320 parts of anhydrous toluene and 2 parts of p-toluenesulfonic acid is stirred and refluxed for 4 hours with water-separator. A second fraction of 30 parts of ethylene glycol is added and stirring at reflux is continued for 18 hours. The reaction mixture is cooled and stirred for 30 minutes with 5 parts of sodium carbonate. The organic layer is separated, washed twice with water, dried and evaporated. The residue is distilled twice, yielding 2-(3-bromo-o-tolyl)-2-methyl-1,3-dioxolane; bp. 148°-150° C at 12 mm. pressure.

Workup

  1. stirringstirring
  2. temperatureat reflux
  3. temperatureThe reaction mixture is cooled
  4. customThe organic layer is separated
  5. washwashed twice with water
  6. customdried
  7. customevaporated
  8. distillationThe residue is distilled twice

Sources & evidence

ORD record
ord-aa07e73ca50745789165111f245b1659
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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