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

HRID 1091221Notes

Reaction equation

HRID 1091221 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-872db2b33d2542f090ee8bc0c2fb14aa
Source dataset
uspto-grants-2012_03
Patent number
US08129039B2

Reaction notes

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