Sodium Sulfate → Citral

HRID 1945250Notes

Reaction equation

HRID 1945250 reaction equation
IC1C=CC=CC=1S([O-])(=O)=O.[Na+].OOS([O-])=O.[K+].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH3:26]/[C:27](/[CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])=[CH:28]\[CH2:29][OH:30]>[N+](C)([O-])=O>[CH3:26]/[C:27](/[CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])=[CH:28]\[CH:29]=[O:30]

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 637566GeraniolHCID 23662047Sodium 2-IodobenzenesulfonateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 638011Citral

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
70 °C

Procedure

6.1 mg (0.02 mmol) of sodium 2-iodobenzenesulfonate prepared by Preparation Example 4, 0.37 g (0.6 mmol) of powdered Oxone (registered trademark), 0.5 g (3.5 mmol) of anhydrous sodium sulfate and 154 mg (1 mmol) of (E)-3,7-dimethylocta-2,6-dien-1-ol were added to 5 ml of nitromethane, and the mixture was heated at 70° C. while being stirred under a nitrogen for two hours. The later treatment was carried out in the same way as in Example 1, and then (E)-3,7-dimethylocta-2,6-dienal was obtained. The yield of the obtained (E)-3,7-dimethylocta-2,6-dienal was determined and the result is shown in Table 2. (Yield: E:Z=16:1)

Sources & evidence

ORD record
ord-f1d3de82320a4deaa4f18892dad51481
Source dataset
uspto-grants-2013_03
Patent number
US08394995B2

Reaction notes

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