Ethylene Glycol → HCID 22601716, compound

HRID 2308247Notes

Reaction equation

HRID 2308247 reaction equation
[Br:1][C:2]1[C:6]([CH3:7])=[C:5]([I:8])[S:4][C:3]=1[CH:9]=[O:10].[CH2:11](O)[CH2:12][OH:13]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[C:6]([CH3:7])=[C:5]([I:8])[S:4][C:3]=1[CH:9]1[O:13][CH2:12][CH2:11][O:10]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 22601706HCID 22601706, compound

Product 1

HCID 22601716HCID 22601716, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

3-Bromo-5-iodo-4-methylthiophene-2-carbaldehyde (27 g, 82 mmol), ethylene glycol (5.9 mL, 110 mmol) and p-toluenesulfonic acid monohydrate (0.50 g, 2.6 mmol) were combined in benzene (200 mL) and the mixture was heated at reflux under Dean-Stark conditions for 8 h. At this time, the cooled solution was washed with 2.5 N aqueous NaOH (200 mL), water (4×200 mL) and brine (200 mL), dried (K2CO3) and concentrated in vacuo to give the title compound (29 g, 94%) as an orange oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 8 h
  3. washAt this time, the cooled solution was washed with 2.5 N aqueous NaOH (200 mL), water (4×200 mL) and brine (200 mL)
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a293618d42c438798e20d405389667a
Source dataset
uspto-grants-2004_12
Patent number
US06835745B2

Reaction notes

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