Ethylene Glycol → HCID 19843450, compound

HRID 2352568Notes

Reaction equation

HRID 2352568 reaction equation
C[O-].[Na+].[CH2:4]([OH:7])[CH2:5][OH:6].Br[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.[I-].[Na+]>[Cu]=O.CO>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[O:6][CH2:5][CH2:4][OH:7]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 5238Sodium IodideHCID 138512-BromothiopheneHCID 10942334Sodium Methoxide

Product 1

HCID 19843450HCID 19843450, compound

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

323.7 ml of 5.4M sodium methylate solution (1.75 mol) are added to 1,600 ml of absolute ethylene glycol. The reaction mixture is heated and the methanol formed is distilled off over a reflux divider, while passing through nitrogen, until the bottom temperature rises to 130° C. When the removal of methanol has ended, 187.5 g (1.15 mol) of 2-bromothiophene, 55.5 g of finely ground copper oxide and 5.6 g of sodium iodide are added, the apparatus is further flushed briefly with nitrogen and closed with a flask and the mixture is stirred at 80° C. for 175 hours.

Workup

  1. temperatureThe reaction mixture is heated
  2. distillationis distilled off over a reflux divider
  3. customrises to 130° C
  4. customWhen the removal of methanol
  5. customthe apparatus is further flushed briefly with nitrogen
  6. customclosed with a flask

Sources & evidence

ORD record
ord-f3201269817548419481be3b527769fb
Source dataset
uspto-grants-1989_10
Patent number
US04877809

Reaction notes

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