Dihydrocoumarin → 4-Hydroxy-1-indanone

HRID 1451326Notes

Reaction equation

HRID 1451326 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[O:11][C:9](=[O:10])[CH2:8][CH2:7][C:5]=2[CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[OH:11][C:4]1[CH:3]=[CH:2][CH:1]=[C:6]2[C:5]=1[CH2:7][CH2:8][C:9]2=[O:10]

Participants

4

Reactant 2

HCID 660DihydrocoumarinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5905474-Hydroxy-1-indanoneYield 41.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
200 °C

Procedure

Dihydrocoumarin (35 g, 0.236 mol) was added to 62.9 g (0.472 mol) of aluminum chloride and the mixture was heated in an oil-bath at 200° C. for 2.5 h with stirring The reaction mixture was cooled, poured into ice (300 g), 300 ml of methylene chloride added to the mixture, cooled, and 400 ml of methylene chloride was added. The mixture was filtered and the solid residue was dissolved in hot methanol, filtered, and the filtrate was cooled to afford 14.5 g (41%) of 4-hydroxy-indan-1-one.

Workup

  1. temperaturewas cooled
  2. additionadded to the mixture
  3. temperaturecooled
  4. filtrationThe mixture was filtered
  5. dissolutionthe solid residue was dissolved in hot methanol
  6. filtrationfiltered
  7. temperaturethe filtrate was cooled

Sources & evidence

ORD record
ord-f7a2d61133be4d6b96617d6ef3f289d9
Source dataset
uspto-grants-1997_02
Patent number
US05604224

Reaction notes

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