Ethylene Glycol → HCID 12941343, compound

HRID 1757948Notes

Reaction equation

HRID 1757948 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 (32.5 g) in benzene (500 ml) was treated with PTSA (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×) 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×)
  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-3b2d56fb446c4dbc8682eaa000cd4411
Source dataset
uspto-grants-1983_02
Patent number
US04371530

Reaction notes

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