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

HRID 2185637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185637
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 112638284-Hydroxy-5-methoxy-1-indanoneAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9834dba787084c689ea84ca6721d8194
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403573B1

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