Ethylene Glycol → 1-Bromo-3-(1,3-dioxolan-2-YL)-4-methoxybenzene

HRID 356630Notes

Reaction equation

HRID 356630 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([O:10][CH3:11])=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][OH:14]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:7]2[O:14][CH2:13][CH2:12][O:8]2)[CH:9]=1

Participants

5

Reactant 2

HCID 174Ethylene Glycol2×HCID 906845-Bromo-2-methoxybenzaldehyde

Product 1

HCID 223495891-Bromo-3-(1,3-dioxolan-2-YL)-4-methoxybenzeneYield 126.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 5-bromo-o-anisaldehyde (49.7 g, 231 mmol), ethylene glycol (17.2 g, 277 mmol) and p-toluene sulfonic acid (4.3 g, 23 mmol) in dry toluene (400 ml) was heated at reflux for 21 hr. And then ethylene glycol (4.3 g, 70 mmol) was added to the reaction mixture and heated at reflux for 6 hr. The resulting solution was washed with sat. NaHCO3, water and brine, dried over MgSO4 and concentrated in vacuo to give crude 2-(5-bromo-2-methoxyphenyl)-1,3-dioxolane (75.7 g) as a dark red oil. The residue was added NaHCO3 and then distilled to give 2-(5-bromo-2-methoxyphenyl)-1,3-dioxolane (52.8 g, 88.3%) as a colorless oil.

Workup

  1. temperatureat reflux for 21 hr
  2. temperatureheated
  3. temperatureat reflux for 6 hr
  4. washThe resulting solution was washed with sat. NaHCO3, water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7ac7d12baa6400592a091f7055f8923
Source dataset
uspto-grants-1998_11
Patent number
US05837711

Reaction notes

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