Ethylene Glycol → HCID 13520040, compound

HRID 484746Notes

Reaction equation

HRID 484746 reaction equation
[N:1]1([CH2:6][C:7]([C:9]2[CH:21]=[CH:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:12][C:11]=3[CH:10]=2)=[O:8])[CH:5]=[CH:4][N:3]=[CH:2]1.C1(C)C=CC=CC=1.[CH2:29](O)[CH2:30][OH:31].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH:10]1[C:11]2[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]=2[CH:20]=[CH:21][C:9]=1[C:7]1([CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[O:31][CH2:30][CH2:29][O:8]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 57350Ethanone, 1-(9H-fluoren-2-yl)-2-(1H-imidazol-1-yl)-

Product 1

HCID 13520040HCID 13520040, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a slurry of 10.0 g. of 2-(1H-imidazol-1-yl)-1-(9H-fluoren-2-yl)ethanone in 100 ml. of toluene were added 4.53 g. of ethylene glycol and 13.9 g. of p-toluenesulfonic acid. The mixture was heated overnight at reflux with the azeotropic removal of water. The reaction was poured into water and the resulting solid was removed by filtration. The solid was basified with 50 percent sodium hydroxide and extracted with ethyl acetate. The ethyl acetate was washed with water, followed by a saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated in vacuo. The residue was crystallized from acetone to provide 8.64 g. of the title product, m.p. 163°-166° C.

Workup

  1. temperatureThe mixture was heated overnight
  2. customthe resulting solid was removed by filtration
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was crystallized from acetone
  9. customto provide 8.64 g

Sources & evidence

ORD record
ord-62eeed945a5d4828931ee66dc2d46d47
Source dataset
uspto-grants-1985_08
Patent number
US04533670

Reaction notes

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