Hydrochloric Acid → 6-Hydroxy-1-indanone

HRID 1277036Notes

Reaction equation

HRID 1277036 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C(C)=CC=CC=1>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3340366-Methoxy-1-IndanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 70206596-Hydroxy-1-indanoneYield 80.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Under argon atmosphere, 6-methoxy-1-indanone (10.0 g) was dissolved in xylene (10 ml), and to the mixture was added aluminum chloride (16.4 g). The mixture was refluxed for 2 hours and then cooled to room temperature. To the mixture was added 3N hydrochloric acid (100 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate) to give 6-hydroxy-1-indanone (7.36 g) as pale brown crystals.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ffae23bcb4984f2b97b7f3aea15f9e35
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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