Benzene → 1-Indanone, 3-phenyl-

HRID 1955288Notes

Reaction equation

HRID 1955288 reaction equation
[C:1]([OH:11])(=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Cl-].[Cl-].[Al+3]>>[C:12]1([CH:3]2[C:4]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:1](=[O:11])[CH2:2]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 87842-Propenoic acid, 3-phenyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 981461-Indanone, 3-phenyl-Yield 600.2%

Procedure

To the solution of 90 g (0.0608 moles) of cinnamic acid in 400 ml of benzene 300 g (2.25 moles) of aluminium trichloride is added, beginning with a very slow addition rate. At the end, the mixture is kept refluxing for 22 hours. The resulting reaction mixture is hydrolysed with ice and is extracted with ethyl ether which is washed first with water until neutral, and then with a solution of 10% sodium hydroxide. The organic extract is then desiccated and evaporated. The residue is triturated with petroleum ether, is then filtered and is then washed with a small amount of diisopropyl ether, then once more with petroleum ether and is dried yielding 76 g (yield of 60%) of 3-phenyl-1-indanone.

Workup

  1. temperatureAt the end, the mixture is kept refluxing for 22 hours
  2. customThe resulting reaction mixture
  3. extractionis extracted with ethyl ether which
  4. washis washed first with water until neutral, and then with a solution of 10% sodium hydroxide
  5. extractionThe organic extract
  6. customevaporated
  7. customThe residue is triturated with petroleum ether
  8. filtrationis then filtered
  9. washis then washed with a small amount of diisopropyl ether
  10. dry with materialonce more with petroleum ether and is dried

Sources & evidence

ORD record
ord-d0c3d931ba224c658bfe0a32ca7657b2
Source dataset
uspto-grants-2000_09
Patent number
US06124413

Reaction notes

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