Acetic Acid → 2,4-diphenylbicyclo[3.3.1]non-2-en-9-one

HRID 990614Notes

Reaction equation

HRID 990614 reaction equation
[C:1]1([CH:7]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=[O:23])[CH2:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.Cl>O>[C:10]1([C:9]2[CH:19]3[C:18](=[O:23])[CH:17]([CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=2)[CH2:22][CH2:21][CH2:20]3)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 2728562-(3-oxo-1,3-diphenylpropyl)cyclohexanone

Product 1

HCID 2728532,4-diphenylbicyclo[3.3.1]non-2-en-9-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1 L round bottom flask fifteen parts of 2-(α-phenyl-β-benzoylethyl)-cyclohexanone, 500 ml acetic acid and 100 mL of concentrated hydrochloric acid was added. Reaction mixture was heated under reflux for 45 hours. The hot reaction mixture was diluted with 250 ml of water (reaction mixture was cloudy). The reaction mixture was cool to room temperature to give a white solid which was filtered and dried under vacuum, to yield 11.75 g of product. The reaction proceeded as follows:

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 45 hours
  4. customto give a white solid which
  5. filtrationwas filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c0549682fa794fd49a53fd68442d29f3
Source dataset
uspto-grants-2002_10
Patent number
US06461876B1

Reaction notes

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