Hydrochloric Acid → 6-Hydroxy-1-indanone

HRID 1387790Notes

Reaction equation

HRID 1387790 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 (100 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-d87970b6d1b44478954ddf840603aa18
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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