Ethylene Glycol → HCID 14770852, compound

HRID 1090389Notes

Reaction equation

HRID 1090389 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)=[C:4]([F:15])[CH:3]=1.[CH2:16](O)[CH2:17][OH:18]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][C:11]3([O:18][CH2:17][CH2:16][O:14]3)[CH2:10]2)=[C:4]([F:15])[CH:3]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 14770833HCID 14770833, compound

Product 1

HCID 14770852HCID 14770852, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 27.5 g (0.1 mol) of 3-(4-bromo-2,5-difluorophenyl)cyclopentanone, 18.6 g (0.3 mol) of ethylene glycol, 1 g of p-toluenesulfonic acid and 500 ml of toluene was heated at reflux with a Dean-Stark trap for 18 hours. The cooled solution was washed with 5% sodium bicarbonate solution (2×250 ml), dried (MgSO4), and evaporated in vacuo to give 28.2 g of the title compound which was used without further purification.

Workup

  1. temperatureat reflux with a Dean-Stark trap for 18 hours
  2. washThe cooled solution was washed with 5% sodium bicarbonate solution (2×250 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-14eaa3df3d894956925cafa05ead8768
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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