1-Hydroxy-5-methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene → 5-Methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-nona-2,6,8-trienal

HRID 1596029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1596029
[OH:1][CH2:2][CH:3]=[C:4]([CH3:23])[CH2:5][CH:6]([O:21][CH3:22])[CH:7]=[C:8]([CH3:20])[CH:9]=[CH:10][C:11]1[C:16]([CH3:18])([CH3:17])[CH2:15][CH2:14][CH2:13][C:12]=1[CH3:19]>C(Cl)Cl.CCOCC.[O-2].[O-2].[Mn+4]>[CH3:22][O:21][CH:6]([CH:7]=[C:8]([CH3:20])[CH:9]=[CH:10][C:11]1[C:16]([CH3:18])([CH3:17])[CH2:15][CH2:14][CH2:13][C:12]=1[CH3:19])[CH2:5][C:4]([CH3:23])=[CH:3][CH:2]=[O:1]

Komponenten

5

Edukt 1

HCID 850402931-Hydroxy-5-methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene

Produkt 1

HCID 850645145-Methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-nona-2,6,8-trienalAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.34 g (4.2 mmol) of 1-hydroxy-5-methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene (IV) was dissolved in 40 ml of methylene chloride, to which was then added 3.66 g (42 mmol) of manganese dioxide and the mixture was stirred at an ambient temperature for 24 hours. After the resulting mixture was diluted with an ether, it was dried over anhydrous magnesium sulfate and filtered, followed by evaporation of the solvent to obtain 5-methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-nona-2,6,8-trienal (V) as a mixture of E and Z isomers in a yield of 91%.

Aufarbeitung

  1. dry with materialwas dried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. customfollowed by evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-e8e7b94d189e4abd86aa6641db6badfe
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288283B1

Notizen zur Reaktion

Wird geladen…