Ethylene Glycol → 2-(4-Bromophenyl)-1,3-dioxolane

HRID 1715519Notes

Reaction equation

HRID 1715519 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12].O>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:12][CH2:11][CH2:10][O:7]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 707414-Bromobenzaldehyde

Product 1

HCID 27738422-(4-Bromophenyl)-1,3-dioxolaneYield 99.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

100 g (540 mmol) of 4-bromobenzaldehyde together with 200 mg of ptoluenesulfonic acid and 30 ml (540 mmol) of anhydrous ethylene glycol are initially introduced in 600 ml of toluene, and the mixture is refluxed on a water separator with monitoring by TLC. When the reaction is complete, the reaction solution is washed twice with sat. NaHCO3 solution and once with water, dried over Na2SO4 and evaporated in a rotary evaporator, giving 123 g (99% of theory) of the dioxolane as a yellow oil.

Workup

  1. washthe reaction solution is washed twice with sat. NaHCO3 solution and once with water
  2. dry with materialdried over Na2SO4
  3. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-b8f0b9dd6dd64b69b5ef50c2eed2dda6
Source dataset
uspto-grants-2010_09
Patent number
US07799875B2

Reaction notes

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