Methanesulfonic Acid → (6R,10R)-6,10,14-trimethylpentadecan-2-one

HRID 844621Notes

Reaction equation

HRID 844621 reaction equation
[CH3:1][C:2](O)([CH2:5][CH2:6][CH:7]=[C:8]([CH3:15])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[C:3]#[CH:4].C[O:18][C:19]([CH3:21])=[CH2:20].CS(O)(=O)=O.CC([O-])=O.[Na+]>CCCCCCC>[CH3:15][C@H:8]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:7][CH2:6][CH2:5][C@H:2]([CH2:3][CH2:4][CH2:20][C:19]([CH3:21])=[O:18])[CH3:1]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 83002-MethoxypropeneHCID 102805DehydronerolidolHCID 517045Sodium Acetate

Product 1

HCID 1810793(6R,10R)-6,10,14-trimethylpentadecan-2-oneYield 76%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

44.1 g 3,7,11-trimethyl-6,10-dodecadien-1-in-3-ol, 50.5 g isopropenyl methyl ether and 80 mL n-heptane were initially introduced into a 500 ml flask. 29 mg methanesulfonic acid were added, while stirring. The reaction mixture was stirred under reflux for 6 hours. After the end of the reaction, the mixture was cooled to room temperature, neutralized with 2.5 ml methanolic NaOAc solution (10 g/1) and evaporated. The residue was hydrogenated in 2-propanol with 10% Pd/A-charcoal. Phytone was obtained in a yield of 76%.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 6 hours
  3. customAfter the end of the reaction
  4. customevaporated

Sources & evidence

ORD record
ord-3bf0d230aa6543949f55e0c7a8591389
Source dataset
uspto-grants-2002_04
Patent number
US06380437B1

Reaction notes

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