methyl 6-(benzyloxy)-alpha-methyl-1H-benzotriazole-1-acetate → methyl 6-hydroxy-alpha-methyl-1H-benzotriazole-1-acetate

HRID 2293728Notes

Reaction equation

HRID 2293728 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[N:15][N:14]([CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])[C:13]=2[CH:23]=1)C1C=CC=CC=1.[H][H]>C(COC)OC.CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[N:15][N:14]([CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])[C:13]=2[CH:23]=1

Participants

6

Reactant 2

HCID 53891908methyl 6-(benzyloxy)-alpha-methyl-1H-benzotriazole-1-acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 136161847methyl 6-hydroxy-alpha-methyl-1H-benzotriazole-1-acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of methyl 6-(benzyloxy)-α-methyl-1H-benzotriazole-1-acetate (31 g, 0.1 mole) in dimethoxyethane and methanol is shaken with 10% palladium on carbon catalyst (8 g, 50% water wet) under 24 -33 psig of hydrogen in a Parr apparatus until approximately 0.1 mole of H2 is absorbed (21/2 hours). The reaction mixture is filtered and the filtrate is concentrated in vacuo to give the title compound as an off-white solid, 21.7 g, mp 132.5°-134.5° C., identified by NMR and elemental analyses.

Workup

  1. customis absorbed (21/2 hours)
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-4c06f9f546e7467bb3646c743fab2014
Source dataset
uspto-grants-1997_11
Patent number
US05686617

Reaction notes

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