3,3-Diphenylacrolein → HCID 54484701, compound

HRID 2211343Notes

Reaction equation

HRID 2211343 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]([CH3:21])([O-])[CH3:19].[K+]>CN(C=O)C>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=[CH:17][C:18]2[CH:21]=[CH:21][C:18]([CH:17]=[CH:9][CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:19][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 710273,3-DiphenylacroleinHCID 23665647Potassium tert-butoxide

Product 1

HCID 54484701HCID 54484701, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 100 ml of DMF were dissolved 5.53 g of 3,3-diphenylacrolein and 5.0 g of p-xylene-α,α'-diylbis(diethyl phosphonate), and 3.87 g of potassium tert-butoxide was added to the solution at room temperature. Thereafter, the reaction was carried out for 4 hours at room temperature with stirring and the reaction mixture was poured into 100 ml of ice-water with stirring. Then, precipitates thus deposited were collected by filtration, dissolved in benzene, and separated and purified by silica gel column chromatography (eluent: benzene). After distilling off benzene from the effluent, the residue was recrystallized from ethyl acetate to provide 1.00 g (yield 15.6%) of yellow crystals having a melting point of from 237.0° C. to 249.5° C.

Workup

  1. additionwas added to the solution at room temperature
  2. stirringwith stirring
  3. customThen, precipitates thus
  4. filtrationdeposited were collected by filtration
  5. dissolutiondissolved in benzene
  6. customseparated
  7. custompurified by silica gel column chromatography (eluent: benzene)
  8. distillationAfter distilling off benzene from the effluent
  9. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5da9809188d443b18428ca1028b1050d
Source dataset
uspto-grants-1995_10
Patent number
US05463128

Reaction notes

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