1,3-Diphenyl-2-propanone → HCID 18618173, compound

HRID 1264146Notes

Reaction equation

HRID 1264146 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=O)=O)=[CH:4][CH:3]=1.[C:19]1([CH2:25][C:26]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)COCCO[CH2:41][CH2:42]O.[OH-].[CH2:46]([N+](C)(C)C)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:26]([C:42]3[CH:41]=[CH:4][CH:3]=[CH:2][CH:7]=3)[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 75931,3-Diphenyl-2-propanoneHCID 8172Triethylene GlycolHCID 66854Benzyltrimethylammonium hydroxideHCID 964304,4'-Dibromobenzil

Product 1

HCID 18618173HCID 18618173, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

46 g (112 mmol) of 4,4′-dibromobenzil and 23.7 g (112 mmol) of 1,3-diphenylacetone were heated to the boiling point in 300 ml of toluene. Addition of 250 ml of triethylene glycol finally gave a clear solution at 120° C. 11.3 ml of ethanolic benzyltrimethylammonium hydroxide solution (40%) were added, and the heating was removed. The highly exothermic reaction proceeded very quickly. The reaction batch became black. After 10 minutes, the reaction was terminated. The toluene was removed in a rotary evaporator, and the solid which remained was filtered off with suction at room temperature and washed a number of times with MeOH. Drying under reduced pressure gave 57 g of brown-violet crystals (94%). Melting point: 245° C.

Workup

  1. customfinally gave a clear solution at 120° C
  2. customthe heating was removed
  3. customThe highly exothermic reaction
  4. customthe reaction was terminated
  5. customThe toluene was removed in a rotary evaporator
  6. filtrationthe solid which remained was filtered off with suction at room temperature
  7. washwashed a number of times with MeOH
  8. customDrying under reduced pressure

Sources & evidence

ORD record
ord-0b620c8bcdd34e87bf0df0e6908a53d8
Source dataset
uspto-grants-2003_04
Patent number
US06541602B1

Reaction notes

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