Acenaphthenequinone → 7,9-Diphenyl-8H-cyclopenta[a]acenaphthylen-8-one

HRID 571586

Reaction equation

HRID 571586 reaction equation
[C:1]1(=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[C:2]1=O.[C:15]1([CH2:21][C:22](=[O:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[K+]>C(O)C>[C:24]1([C:23]2[C:22](=[O:30])[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:2]3[C:3]4=[C:12]5[C:7](=[CH:6][CH:5]=[CH:4]4)[CH:8]=[CH:9][CH:10]=[C:11]5[C:1]=23)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6724AcenaphthenequinoneHCID 75931,3-Diphenyl-2-propanoneHCID 14797Potassium Hydroxide2×

Product 1

HCID 2671457,9-Diphenyl-8H-cyclopenta[a]acenaphthylen-8-oneYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

An amount of 5.9 g (32.4 mmol) of acenaphthenequinone and 7.5 g (35.7 mmol) of 1,3-diphenyl-2-propanone were suspended in 150 ml of ethanol and a solution of 2 g of potassium hydroxide in ethanol was added. After the mixture was heated to the reflux temperature, the same amount of the solution of potassium hydroxide in ethanol was further added and allowed to react for five minutes. The solid substance deposited after cooled on ice was filtered and washed with ethanol to obtain 8.24 g (23.1 mmol) of 7,9-diphenylcyclopenta[a]acenaphthylene-8-one. The yield was 71.3%.

Workup

  1. temperatureAfter the mixture was heated to the reflux temperature
  2. customto react for five minutes
  3. temperatureThe solid substance deposited after cooled on ice
  4. filtrationwas filtered
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-67ff0ccdf2d04779ba9e16d21b7f7d1e
Source dataset
uspto-grants-2015_05
Patent number
US09028976B2

Linked notes

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