1,3-Diphenyl-2-propanone → HCID 59594059, compound

HRID 657461Notes

Reaction equation

HRID 657461 reaction equation
[C:1]1([CH2:7][C:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17][C:18]1[C:28]2[C:29]3[C:21]([C:22](=O)[C:23](=O)[C:24]=3[CH:25]=[CH:26][CH:27]=2)=[CH:20][CH:19]=1.[OH-].[K+]>CO>[Br:17][C:18]1[CH:19]=[CH:20][C:21]2=[C:29]3[C:28]=1[CH:27]=[CH:26][CH:25]=[C:24]3[C:23]1[C:22]2=[C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8](=[O:9])[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 75931,3-Diphenyl-2-propanoneHCID 14797Potassium HydroxideHCID 111730241,2-Acenaphthylenedione, 5-bromo-

Product 1

HCID 59594059HCID 59594059, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

1,3-Diphenylacetone (17.5 g, 83 mMole) was dissolved in methanol (240 mL) and heated to 65° C. To the solution was added 5-bromoacenaphthenequinone (2), (20 g, 75 mMole). The resulting well-stirred suspension was then treated with 1M-methanolic KOH (100 mL, 100 mMole) at a fast drip rate, whereupon the dark colored product precipitated immediately. The mixture was then stirred at 65° C. for 1 hour, cooled and filtered. The black solid was washed well with methanol, ether and dried. Yield of product (3), (31 g).

Workup

  1. customprecipitated immediately
  2. stirringThe mixture was then stirred at 65° C. for 1 hour
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe black solid was washed well with methanol, ether
  6. customdried

Sources & evidence

ORD record
ord-d7ba39214bd14c88923ac332b07782df
Source dataset
uspto-grants-2011_12
Patent number
US08076009B2

Reaction notes

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