1,3-Diphenyl-2-propanone → HCID 86684982, compound

HRID 511738Notes

Reaction equation

HRID 511738 reaction equation
C1C2[C:15]3=[C:16]4[C:11](=CC=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[C:5]2[C:17](=[O:20])[C:18](=O)[C:3](=[C:4]23)C=1.[C:21]1([CH2:27][C:28]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=O)[CH:26]=[CH:25][CH:24]=[CH:23]C=1.[OH-].[K+].C(O)C.[C:42]1(C)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[C:31]1([C:30]2[C:3]3=[C:18]4[C:25]5=[C:24]6[C:23]7[C:15]([CH:4]=[C:26]5[C:21]3=[CH:27][CH:28]=2)=[CH:16][CH:11]=[CH:10][C:9]=7[CH:8]=[CH:7][C:6]6=[C:5]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:17]4=[O:20])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 75931,3-Diphenyl-2-propanoneHCID 14797Potassium HydroxideHCID 21863594Toluene ethanolHCID 86001546HCID 86001546, compound

Product 1

HCID 86684982HCID 86684982, compound

Conditions

Temperature
50 °C

Procedure

Next, 3 g (11 mmol) of cyclopenta[cd]pyrene-3,4-dione and 2.3 g (11 mmol) of 1,3-diphenylacetone were added to 300 mL of an ethanol/toluene (10/1) solution. Under stirring, 52 mL of 6 N aqueous potassium hydroxide was added dropwise thereto. After the completion of the dropwise addition, the mixture was heated to 50° C., stirred for 1 hour, and cooled. The resulting precipitate was filtered, washed with water, ethanol, and isopropyl alcohol, in that order, and dried by heating under reduced pressure to give 2.85 g of 9,11-diphenyl-10H-pentaleno[1,2,3-cd]pyren-10-one as a black solid.

Workup

  1. additionAfter the completion of the dropwise addition
  2. stirringstirred for 1 hour
  3. temperaturecooled
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water, ethanol, and isopropyl alcohol, in that order
  6. customdried
  7. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-854266ef6fe9460eb8e062902c0e0f75
Source dataset
uspto-grants-2015_08
Patent number
US09099656B2

Reaction notes

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