Water → 5-Hydroxy-1-indanone

HRID 1163284Notes

Reaction equation

HRID 1163284 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[Cl-].[Al+3].[Cl-].[Cl-].O>C1(C)C=CC=CC=1>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 787875-Methoxyindan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2331475-Hydroxy-1-indanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 5-methoxy-1-indanone (10.3 g, 63.5 mmol) in toluene (150 mL) was ice-cooled, and aluminum chloride (16.9 g, 127 mmol) was added by small portions, and the mixture was heated under reflux under nitrogen atmosphere for 4 hr. The reaction mixture was allowed to cool to room temperature and poured into iced water. The organic product was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 5-hydroxy-1-indanone as yellow crystals.

Workup

  1. temperaturecooled
  2. temperaturethe mixture was heated
  3. temperatureunder reflux under nitrogen atmosphere for 4 hr
  4. extractionThe organic product was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e9b349af31b456099d673a82e759c5d
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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