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

HRID 844620Notes

Reaction equation

HRID 844620 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+]>>[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

5

Reactant 4

HCID 6395Methanesulfonic AcidHCID 83002-MethoxypropeneHCID 1026523,7,11-Trimethyldodecyn-3-olHCID 517045Sodium Acetate

Product 1

HCID 1810793(6R,10R)-6,10,14-trimethylpentadecan-2-oneYield 87%

Procedure

44.9 g 3,7,11-trimethyl-1-dodecin-3-ol and 50.5 g isopropenyl methyl ether were initially introduced into a 300 ml V4A steel autoclave with a temperature probe, sampler and pressure indicator. 19 mg methanesulfonic acid were added, while stirring. The autoclave was forced up to 2 bar with nitrogen. The mixture was stirred at 90 to 95° C. for 8 hours. After cooling, the reaction mixture was neutralized with 1.7 ml methanolic NaOAc solution (10 g/1). After evaporation, the crude product was hydrogenated in 2-propanol with 10% Pd/A-charcoal. Phytone was obtained in a yield of 87%.

Workup

  1. stirringThe mixture was stirred at 90 to 95° C. for 8 hours
  2. temperatureAfter cooling
  3. customAfter evaporation

Sources & evidence

ORD record
ord-e05cee0cf1e648b0b9defa83cc7d2b6e
Source dataset
uspto-grants-2002_04
Patent number
US06380437B1

Reaction notes

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