1-[4-(4-Benzyloxyphenyl)butyl]-1,2,4-triazole → 1-[4-(4-Hydroxyphenyl)butyl]-1,2,4-triazole

HRID 322256Notes

Reaction equation

HRID 322256 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[C].[Pd].C(O)C>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 220098341-[4-(4-Benzyloxyphenyl)butyl]-1,2,4-triazole

Product 1

HCID 220096301-[4-(4-Hydroxyphenyl)butyl]-1,2,4-triazoleYield 55%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-[4-(4-benzyloxyphenyl)butyl]-1,2,4-triazole (3.15 g), palladium-carbon (5%, 3.0 g) and ethanol (50 ml) was subjected to catalytic hydrogenation under atmospheric pressure at room temperature. The catalyst was filtered off, and the filtrate was concentrated. The residue was subjected to a silica gel column chromatography. The crystalline product obtained from the fraction eluted with tetrahydrofuran-hexane (1:1, v/v) was recrystallized from ethyl acetate-hexane to give 1-[4-(4-hydroxyphenyl)butyl]-1,2,4-triazole (1.22 g, 55%) as colorless prisms, mp 135-136° C.

Workup

  1. customwas subjected to catalytic hydrogenation under atmospheric pressure at room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe crystalline product obtained from the fraction
  5. washeluted with tetrahydrofuran-hexane (1:1
  6. customv/v) was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-48e1fa762fb7461fb53c2c44b99a5ac7
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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