Potassium Permanganate → HCID 12942706, compound

HRID 848726Notes

Reaction equation

HRID 848726 reaction equation
[CH3:1][Si:2]([CH3:18])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[Mn]([O-])(=O)(=O)=[O:20].[K+]>N1C=CC=CC=1>[CH3:18][Si:2]([CH3:1])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][CH2:5][C:6]([OH:20])=[O:7]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 12942705HCID 12942705, compound

Product 1

HCID 12942706HCID 12942706, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 25.0 g (91.7 mmol; 366.8 electron equivalents) of 5,5-dimethyl-5-sila-n-pentadecanol in 100 ml of pyridine, is added 21.5 g (136 mmol; 408 electron equivalents) of potassium permanganate in 320 ml of pyridine, at 20°-25° with stirring, and stirring is continued for 30 hr. A dark brown precipitate forms which is filtered off (leaving a colorless filtrate). The filter cake is thoroughly washed with methanol and ligroine. The washes and filtrate are combined and concentrated to near dryness. The residue is added to a mixture of water, ice, petroleum ether and dilute hydrochloric acid and the organic phase recovered. The aqueous phase is washed once with petroleum ether, which wash is then combined with the previously recovered organic phase, and the combined organic phases washed thrice with water, dried, and then concentrated to obtain crude title product, which is refined by distillation through a Vigreux column, b.p. 142°-132° at 0.145-0.115 mm Hg.

Workup

  1. stirringstirring
  2. filtrationA dark brown precipitate forms which is filtered off (
  3. customleaving a colorless filtrate)
  4. washThe filter cake is thoroughly washed with methanol and ligroine
  5. concentrationconcentrated
  6. additionThe residue is added to a mixture of water, ice, petroleum ether and dilute hydrochloric acid
  7. customthe organic phase recovered
  8. washThe aqueous phase is washed once with petroleum ether, which
  9. washwash
  10. washthe combined organic phases washed thrice with water
  11. customdried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-6783d0df48ea4f38a12c10f0cd95bb93
Source dataset
uspto-grants-1981_10
Patent number
US04297349

Reaction notes

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