Methanesulfonic Acid → HCID 20306810, compound

HRID 1764169Notes

Reaction equation

HRID 1764169 reaction equation
CS(O)(=O)=O.[H][H].[CH3:8][C:9]([O:16][O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH2:11][CH2:12][C:13](=[O:15])[CH3:14])[CH3:10]>[Pt]>[CH3:10][C:9]([O:16][O:17][C:18]([CH3:19])([CH3:21])[CH3:20])([CH2:11][CH2:12][CH:13]([OH:15])[CH3:14])[CH3:8]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 20306806HCID 20306806, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20306810HCID 20306810, compound

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

The catalytic hydrogenation of the carbonyl group in 2-methyl-2-(t-butylperoxy)-5-hexanone was carried out by shaking 5.0 g. (0.025 mole) of the ketone in a Parr Hydrogenation Apparatus with 25 ml. of 10% methanesulfonic acid solution and 1.0 g. of 5% platinum on carbon catalyst at 0° C. for 2 1/2 hours with a hydrogen pressure of 60 p.s.i.g. At the end of the reaction time, the catalyst was separated by filtration, the product taken up in 50 ml. of pentane, the pentane solution washed to neutrality with water, dried over anhydrous magnesium sulfate and the pentane removed under reduced pressure. The recovered product weighed 3.3 g. (65% recovery). An infrared spectrum showed the presence of a hydroxyl band and the absorption band at 880 cm-1 typical of the t-butylperoxy group.

Workup

  1. customat 0° C.
  2. customfor 2 1/2 hours
  3. customAt the end of the reaction time, the catalyst was separated by filtration
  4. washof pentane, the pentane solution washed
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe pentane removed under reduced pressure

Sources & evidence

ORD record
ord-cbcd5c01afce4b0b8dd1363e74102920
Source dataset
uspto-grants-1978_09
Patent number
US04115455

Reaction notes

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