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

HRID 1970752Notes

Reaction equation

HRID 1970752 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-52214ed8e9bc4dee8c5c80e1cc0dbaf4
Source dataset
uspto-grants-2013_04
Patent number
US08431242B2

Reaction notes

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