Ethylene Glycol → HCID 12941343, compound

HRID 1903708Notes

Reaction equation

HRID 1903708 reaction equation
Br[C:2]1[S:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.[CH2:9]([OH:12])[CH2:10]O.O.[CH:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC1C=CC(S(O)(=O)=O)=CC=1>[O:12]1[CH2:9][CH2:10][O:8][CH:7]1[C:4]1[CH:3]=[C:2]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:6][CH:5]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 962WaterHCID 122848945-Bromothiophene-3-carbaldehyde

Product 1

HCID 12941343HCID 12941343, compound

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A solution of 5-bromo-3-thiophenecarboxaldehyde (32.5g) in benzene (500 ml) was treated with PTSA (0.323g) and ethylene glycol (21.1g), and the mixture heated under reflux in a Dean and Stark apparatus until the theoretical volume of water had been removed. After cooling the mixture was washed with water, (2x) then brine, dried (MgSO4), filtered and concentrated, and the residue distilled (b.p. 96°-100° at 0.4 mm) to give the title compound as an oil (24 g).

Workup

  1. temperaturethe mixture heated
  2. customhad been removed
  3. temperatureAfter cooling the mixture
  4. washwas washed with water, (2x)
  5. dry with materialbrine, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. distillationthe residue distilled (b.p. 96°-100° at 0.4 mm)

Sources & evidence

ORD record
ord-0a1c996ec206469e916003eb6c47003d
Source dataset
uspto-grants-1984_03
Patent number
US04438111

Reaction notes

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