Ethylene Glycol → 2-(3-Bromothiophen-2-yl)-1,3-dioxolane

HRID 1611598Notes

Reaction equation

HRID 1611598 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[CH2:9](O)[CH2:10][OH:11].C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[O:11][CH2:10][CH2:9][O:8]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 27970793-Bromothiophene-2-carboxaldehyde

Product 1

HCID 122202112-(3-Bromothiophen-2-yl)-1,3-dioxolaneYield 74.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Bromothiophen-2-aldehyde (2) (7.44 g, 39 mmol), ethylene glycol (2.7 ml, 48 mmol), anhydrous benzene (130 ml) and a few crystals of p-toluenesulphonic acid were refluxed in a Dean-Stark apparatus until no more water separated. The benzene layer was washed with a solution of bicarbonate, dried (Na2SO4), and evaporated under reduced pressure to give the derivative 3 (6.8 g, 28.9 mmol, 74% yield) as an oil.

Workup

  1. customseparated
  2. washThe benzene layer was washed with a solution of bicarbonate
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c59592d4ef474d38b102812fe8c1612e
Source dataset
uspto-grants-2006_01
Patent number
US06989388B2

Reaction notes

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