Ethylene Glycol → HCID 12941343, compound

HRID 2286191Notes

Reaction equation

HRID 2286191 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>O.C1(C)C=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 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

A solution of 5-bromo-3-thiophenecarboxaldehyde (32.5 g) in benzene (500 ml) was treated with p-toluenesulphonic acid monohydrate (0.323 g) and ethylene glycol (21.1 g), 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, (2 x) then brine, dried, 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, (2 x)
  5. dry with materialbrine, dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. distillationthe residue distilled (b.p. 96°-100° at 0.4 mm)

Sources & evidence

ORD record
ord-93f266e7b122460e9f04c6c781695207
Source dataset
uspto-grants-1982_04
Patent number
US04327092

Reaction notes

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