Ethylene Glycol → HCID 22341453, compound

HRID 584918Notes

Reaction equation

HRID 584918 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6](C2C=CC=CC=2)=[CH:5][C:4]=1[CH2:15][NH:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.[C:25]1([CH3:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:32]([OH:35])[CH2:33][OH:34]>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[O:34]1[CH2:33][CH2:32][O:35][CH:31]1[C:25]1[CH:30]=[CH:29][C:28]([C:6]2[CH:7]=[CH:8][CH:3]=[C:4]([CH2:15][NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:5]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 22341509HCID 22341509, compound

Product 1

HCID 22341453HCID 22341453, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

3.2 g (10 mmol) of N-(4-formylbiphenyl-3-yl-methyl)benzamide, 50 ml of toluene, 2.8 ml (50 mmol) of ethylene glycol and 38 mg (0.2 mmol) of para-toluenesulfonic acid are introduced into a three-necked flask under a stream of nitrogen. The reaction medium is refluxed for 3 hours and the water formed is separated off using Dean-stark apparatus. The reaction medium is extracted with dichloromethane and washed with water, and the organic phase is separated out after settling of the phases has taken place. The organic phase is dried over magnesium sulfate and filtered. 3.7 g (100%) of the desired product are obtained.

Workup

  1. temperatureThe reaction medium is refluxed for 3 hours
  2. customis separated off
  3. extractionThe reaction medium is extracted with dichloromethane
  4. washwashed with water
  5. customthe organic phase is separated out
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-0337c3ef9e6846139526e0ae68d8f366
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

Loading…