HCID 13107025, compound → 2,6-Di-tert-butyl-4-(5-methyl-1H-imidazol-4-yl)phenol

HRID 980341Notes

Reaction equation

HRID 980341 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[NH:17][C:18](=S)[NH:19][C:20]=2[CH3:21])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>[Ni].C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[CH:18][NH:19][C:20]=2[CH3:21])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 13107025HCID 13107025, compound

Product 1

HCID 159146172,6-Di-tert-butyl-4-(5-methyl-1H-imidazol-4-yl)phenolYield 74.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.5 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyl-2-thioxo-4-imidazoline, 0.5 g of a Raney nickel catalyst, and 50 ml of absolute ethanol was refluxed for one hour and after filtering the reaction mixture, the filtrate was concentrated under reduced pressure. The residue was recrystallized from a mixture of cyclohexane and n-hexane to provide 1 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methylimidazole.

Workup

  1. temperaturewas refluxed for one hour
  2. filtrationafter filtering the reaction mixture
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was recrystallized from a mixture of cyclohexane and n-hexane

Sources & evidence

ORD record
ord-6f6d2261fb2c4c7bb246a48d46aa6138
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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