Ethylene Glycol → HCID 21313213, compound

HRID 1679130Notes

Reaction equation

HRID 1679130 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[Br:10]Br.CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1.[CH2:29]([OH:32])[CH2:30]O>O>[Br:10][CH2:8][C:7]1([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[O:32][CH2:29][CH2:30][O:9]1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 24408BromineHCID 805722-Acetyl-5-chlorothiophene

Product 1

HCID 21313213HCID 21313213, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

57 Parts of 1-(5-chloro-2-thienyl)-1-ethanone are dissolved in 220 parts of 1,2-ethanediol at 50° C. While stirring, there are added dropwise, during a 1 hour-period, 64 parts of bromine without external heating. After stirring for 1 hour at room temperature, 4 parts of 4-methylbenzenesulfonic acid and 360 parts of benzene are added. The whole is stirred and refluxed overnight with water-separator. The reaction mixture is evaporated and the residue is taken up in 2,2'-oxybispropane. The resulting solution is washed successively once with a diluted sodium hydroxide solution and three times with water, dried, filtered and evaporated. The residue is distilled, yielding 73.3 parts (64.5%) of 2-(bromomethyl)-2-(5-chloro-2-thienyl)-1,3-dioxolane; bp. 125° -127° C. at 0.1 mm. pressure.

Workup

  1. stirringAfter stirring for 1 hour at room temperature
  2. stirringThe whole is stirred
  3. customThe reaction mixture is evaporated
  4. washThe resulting solution is washed successively once with a diluted sodium hydroxide solution and three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue is distilled

Sources & evidence

ORD record
ord-1daf4b2775fc46a6994c593dcc6a1360
Source dataset
uspto-grants-1978_03
Patent number
US04079062

Reaction notes

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