4,5-Dimethoxy-1-indanone → 4-Hydroxy-5-methoxy-1-indanone

HRID 2185637Notes

Reaction equation

HRID 2185637 reaction equation
C[O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:14].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[OH:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:14]

Participants

4

Reactant 2

HCID 2404464,5-Dimethoxy-1-indanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 112638284-Hydroxy-5-methoxy-1-indanoneYield 69.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere 2,3-dihydro-4,5-dimethoxy-1H-inden-1-one (31.7 g) was dissolved in 600 ml of anhydrous 1,2-dichloroethane and cooled to 0° C. Aluminum chloride (44 g) was added in portions and the reaction mixture was heated to 60° C. for 17 hours, cooled to room temperature and poured into ice/water. After extraction with dichloromethane the organic layer was dried and evaporated. The residue was crystallized from ethyl acetate to give 20.5 g of 2,3-dihydro-4-hydroxy-5-methoxy-1H-inden-1-one, M.S. (C.I.) (M/Z): 179 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated to 60° C. for 17 hours
  2. temperaturecooled to room temperature
  3. extractionAfter extraction with dichloromethane the organic layer
  4. customwas dried
  5. customevaporated
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9834dba787084c689ea84ca6721d8194
Source dataset
uspto-grants-2002_06
Patent number
US06403573B1

Reaction notes

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