5-Methoxyindan-1-one → 5-Hydroxy-1-indanone

HRID 974776Notes

Reaction equation

HRID 974776 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.[Al+3].[Cl-].[Cl-].[Cl-]>C1C=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

4

Reactant 2

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

Product 1

HCID 2331475-Hydroxy-1-indanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5-methoxy-1-indanone (2 g, 12.3 mmol) in benzene (50 ml) was added AlCl3 (4 g, 31 mmol). The mixture was heated at reflux for 5 hours and extracted with ethyl acetate. The organic phase was evaporated and purified by flash chromatography, eluting with CH2Cl2 /CH3CN (90/10) to give 5-hydroxy-1-indanone as a yellow solid (1.65 g; 90%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was evaporated
  5. custompurified by flash chromatography
  6. washeluting with CH2Cl2 /CH3CN (90/10)

Sources & evidence

ORD record
ord-98135e2975c64ab4979da6ff516dcae1
Source dataset
uspto-grants-1997_03
Patent number
US05607928

Reaction notes

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