Ethylene Glycol → 2-(4-Bromo-3,5-dimethoxyphenyl)-1,3-dioxolane

HRID 24702Notes

Reaction equation

HRID 24702 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[CH2:14](O)[CH2:15][OH:16].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:15]1[O:16][CH:6]([C:5]2[CH:8]=[C:9]([O:10][CH3:11])[C:2]([Br:1])=[C:3]([O:12][CH3:13])[CH:4]=2)[O:7][CH2:14]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 30155794-Bromo-3,5-dimethoxybenzaldehyde

Product 1

HCID 142874802-(4-Bromo-3,5-dimethoxyphenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-bromo-3,5-dimethoxybenzaldehyde (3 g) was dissolved in toluene (50 mL) and ethylene glycol (6.8 mL) and a catalytic amount of p-TSA were added. The mixture was refluxed overnight using a Dean Stark apparatus and evaporated. The residue was purified by column chromatography (silica gel; eluent hexane/AcOEt 5:1 to 2:1) to give 4-bromo-3,5-dimethoxybenzaldehyde ethylene acetal (2.63 g).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customevaporated
  3. customThe residue was purified by column chromatography (silica gel; eluent hexane/AcOEt 5:1 to 2:1)

Sources & evidence

ORD record
ord-de1d148024c34b86ba9977e3ecddc571
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

Loading…