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

HRID 2106029Notes

Reaction equation

HRID 2106029 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[CH:5]=1)=[O:3].[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Br:10][C:6]1[CH:5]=[C:4]([C:2]2([CH3:1])[O:13][CH2:12][CH2:11][O:3]2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 174Ethylene Glycol2×HCID 962WaterHCID 165023'-BromoacetophenoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 109992182-(3-Bromophenyl)-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-bromoacetophenone (10 mL, 75.6 mmol), ethylene glycol (10.1 mL, 181 mmol), and p-toluenesulfonic acid hydrate in toluene (120 mL) was heated with azeotropic removal of water. After 4 hours, a second portion of ethylene glycol was added and the mixture heated at refluxed for 48 hours. The reaction was cooled to room temperature and washed with saturated aqueous sodium bicarbonate solution and brine, and dried over sodium sulfate. Removal of the volatiles in vacuo provided a residue that was purified by flash chromatography. Concentration of the product-rich fractions afforded 2-(3-bromophenyl)-2-methyl-[1,3]dioxolane as a clear oil. Yield: 2.44 g.

Workup

  1. temperaturethe mixture heated
  2. temperatureat refluxed for 48 hours
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the volatiles in vacuo
  6. customprovided a residue that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3532de5c33564cdb8a6afb7a65fe0690
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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