Potassium Permanganate → alpha,alpha-Bis(p-tert.-butylphenyl)imidazole-2-methanol

HRID 261956Notes

Reaction equation

HRID 261956 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=2)([C:13]2[N:14](C=C)[CH:15]=[CH:16][N:17]=2)[OH:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=O.[K+]>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=2)([C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)[OH:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 516875Potassium Permanganate2×HCID 12433927alpha,alpha-Bis(p-tert.-butylphenyl)-1-vinylimidazole-2-methanol

Product 1

HCID 12433848alpha,alpha-Bis(p-tert.-butylphenyl)imidazole-2-methanol

Procedure

This compound was prepared by the procedure indicated in Example XXII B using 8 g. (0.02 mol) of α,α-bis(p-tert.-butylphenyl)-1-vinylimidazole-2-methanol, 250 ml. of 4% potassium permanganate solution and 3.3 g. of solid potassium permanganate (total permanganate 0.08 mol). After removal of manganese dioxide and excess permanganate, the organic solvents were distilled off and the remaining liquid was poured into water. A precipitate was formed, which was filtered off and crystallised from a mixture of isopropyl alcohol and petroleum ether (boiling range 28°-40° C.). Melting point 215°-216° C.

Workup

  1. customThis compound was prepared by the procedure
  2. customAfter removal of manganese dioxide and excess permanganate
  3. distillationthe organic solvents were distilled off
  4. additionthe remaining liquid was poured into water
  5. customA precipitate was formed
  6. filtrationwhich was filtered off
  7. customcrystallised from a mixture of isopropyl alcohol and petroleum ether (boiling range 28°-40° C.)

Sources & evidence

ORD record
ord-022dd570a35248f4a235b6d82b7f5ebe
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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