Ethylene Glycol → 2-(2-Bromoethyl)-2-phenyl-1,3-dioxolane

HRID 344282Notes

Reaction equation

HRID 344282 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([OH:15])[CH2:13][OH:14].[Br:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O>C1C=CC=CC=1>[CH2:13]1[CH2:12][O:15][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([CH2:18][CH2:17][Br:16])[O:14]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 1224323-Bromo-1-phenylpropan-1-one

Product 1

HCID 137641292-(2-Bromoethyl)-2-phenyl-1,3-dioxolaneYield 49.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Toluenesulfonic acid in a catalytic amount and ethylene glycol (2.9 g) were added to a solution of 3-bromo-1-phenyl-1-propanone (10 g) in benzene (100 ml), and the mixture was stirred at refluxing temperature for 70 hr. The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 6.0 g of 3,3-ethylenedioxy-3-phenylpropyl bromide.

Workup

  1. temperatureat refluxing temperature for 70 hr
  2. washThe reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3d1639f71d7a442cb18d5a4ee01ed1b6
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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