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

HRID 844619Notes

Reaction equation

HRID 844619 reaction equation
[CH3:1][C:2](O)([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH: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 Acid2×HCID 83002-Methoxypropene2×HCID 1026523,7,11-Trimethyldodecyn-3-olHCID 517045Sodium Acetate

Product 1

HCID 1810793(6R,10R)-6,10,14-trimethylpentadecan-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

56.1 g 3,7,11-trimethyl-1-dodecin-3-ol, 27.0 g isopropenyl methyl ether and 100 mL n-heptane were initially introduced into a 500 ml flask. 14.5 mg methanesulfonic acid were added, while stirring. The reaction mixture was stirred under reflux for 7.5 hours. During this period of time, 36.5 g isopropenyl methyl ether and 21.6 mg methanesulfonic acid were added in each case in two portions. The mixture was cooled to room temperature, neutralized with 3 ml methanolic NaOAc solution (10 g/1) and evaporated. The crude was hydrogenated with 10% Pd/C in isopropanol. Phytone was obtained in a yield of 91%.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 7.5 hours
  3. customevaporated

Sources & evidence

ORD record
ord-f89e01bea90145e182ded014eb8b97a5
Source dataset
uspto-grants-2002_04
Patent number
US06380437B1

Reaction notes

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