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

HRID 1596027Notes

Reaction equation

HRID 1596027 reaction equation
[OH:1][CH2:2][CH:3]=[C:4]([CH3:22])[CH2:5][CH:6]([OH:21])[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]>[OH: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]([CH3:22])=[CH:3][CH:2]=[O:1]

Participants

5

Reactant 1

HCID 853942541,5-Dihydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene

Product 1

HCID 850498895-Hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-nona-2,6,8-trienalYield 90%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1.22 g (4 mmol) of 1,5-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene (I) was dissolved in 30 ml of methylene chloride, to which was then added 3.48 g (40 mmol) of manganese dioxide and the mixture was stirred at an ambient temperature for 24 hours. After the resulting mixture was diluted with ether, it is dried over anhydrous magnesium sulfate and filtered, followed by evaporation of ether to obtain 5-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-nona-2,6,8-trienal (II) as a mixture of E and Z isomers in a yield of 90%.

Workup

  1. dry with materialis dried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. customfollowed by evaporation of ether

Sources & evidence

ORD record
ord-50df49b740ef410da1389bb2db0f4a41
Source dataset
uspto-grants-2001_09
Patent number
US06288283B1

Reaction notes

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