1,1-Ethanediol → 1,3-Dioxolane, 2-(2-bromo-5-methoxyphenyl)-

HRID 1383378Notes

Reaction equation

HRID 1383378 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH:12](O)([OH:14])[CH3:13]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]1[O:14][CH2:12][CH2:13][O:5]1

Participants

5

Reactant 2

HCID 1512111,1-EthanediolHCID 3444802-Bromo-5-methoxybenzaldehyde

Product 1

HCID 111845031,3-Dioxolane, 2-(2-bromo-5-methoxyphenyl)-Yield 98.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-5-methoxybenzaldehyde (5.0 g, 23.2 mmol) in toluene (300 mL) was added ethanediol (2.16 g, 34.2 mmol) and p-TsOH (20 mg), whereafter the mixture was refluxed for 12 hours. The resulting mixture was cooled to room temperature, washed with NaHCO3/aq, dried (Na2SO4), and concentrated to yield 5.918 g (98%) of the sub-title compound.

Workup

  1. temperaturewhereafter the mixture was refluxed for 12 hours
  2. washwashed with NaHCO3/aq
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3c7687d32617410c8d76fe2be590cb0b
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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