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 1596029Notes

Reaction equation

HRID 1596029 reaction equation
[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]

Participants

5

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-e8e7b94d189e4abd86aa6641db6badfe
Source dataset
uspto-grants-2001_09
Patent number
US06288283B1

Reaction notes

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