Cinnamoylbenzene → 3,4,6-Triphenyloxan-2-one

HRID 261037Notes

Reaction equation

HRID 261037 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([C:24]#N)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([OH:28])C.[OH-].[K+]>CCCCCC>[C:18]1([CH:17]2[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10][C:24]2=[O:28])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7189CinnamoylbenzeneHCID 8794PhenylacetonitrileHCID 21946426Potassium hydroxide ethanol

Product 1

HCID 203958933,4,6-Triphenyloxan-2-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

20.8 g (0.1 mol) of chalcone (1,3-diphenyl 1-propenone) are dissolved hot in 12.0 g (0.102 mol) of benzyl cyanide. 60 ml of hexane-absolute alcohol mixture (20-80) are added; the reaction medium is cooled to 0° C. in an ice-salt mixture. The catalyst (8 ml of 2 N ethanol KOH) is then added slowly. Crystallisation intervenes very quickly in the vessel, about 1 hour after the beginning of pouring which lasts 3/4 of an hour. The vessel is then placed in the refrigerator for the night.

Workup

  1. customCrystallisation intervenes very quickly in the vessel, about 1 hour after the beginning
  2. additionof pouring which
  3. custom3/4 of an hour

Sources & evidence

ORD record
ord-8ec93865fefd40039cdb1980af72a991
Source dataset
uspto-grants-1979_08
Patent number
US04163799

Reaction notes

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