1-[3-(benzyloxy)phenyl]-1H-1,2,4-triazole → 3-(1H-1,2,4-triazol-1-yl)phenol

HRID 1798803Notes

Reaction equation

HRID 1798803 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[N:15]1([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)[CH:19]=[N:18][CH:17]=[N:16]1

Participants

4

Reactant 1

HCID 581285101-[3-(benzyloxy)phenyl]-1H-1,2,4-triazole

Product 1

HCID 545929613-(1H-1,2,4-triazol-1-yl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-[3-(benzyloxy)phenyl]-1H-1,2,4-triazole (250 mg, 0.995 mmol) was dissolved in 5 mL methanol. The solution was degassed and backfilled with nitrogen. Palladium on carbon (10% w/w, 106 mg, 0.1 mmol) was then added. The reaction vessel was degassed and backfilled with hydrogen 3 times and stirred under a hydrogen balloon at room temperature. The reaction was stirred overnight. It was then diluted with 5 mL acetone and filtered through a plug of silica gel (5 g), which was washed thoroughly with acetone. Concentration afforded the product as white solid. LRMS calc: 161.1; obs: 162.2 (M+1).

Workup

  1. customThe solution was degassed
  2. customThe reaction vessel was degassed
  3. stirringThe reaction was stirred overnight
  4. additionIt was then diluted with 5 mL acetone
  5. filtrationfiltered through a plug of silica gel (5 g), which
  6. washwas washed thoroughly with acetone
  7. concentrationConcentration

Sources & evidence

ORD record
ord-3309f65a2df64186bf626c4e292ed9fa
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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