2-Methyl-3-nitrobenzyl alcohol → (3-Amino-2-methylphenyl)methanol

HRID 1656925Notes

Reaction equation

HRID 1656925 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]>C(O)C.[Pd].[C]>[NH2:10][C:9]1[C:2]([CH3:1])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH2:4][OH:5]

Participants

4

Reactant 1

HCID 902892-Methyl-3-nitrobenzyl alcohol

Product 1

HCID 577175(3-Amino-2-methylphenyl)methanolYield 87%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of 203 g of 2-methyl-3-nitrobenzyl alcohol in 1000 ml of ethanol is hydrogenated in the presence of 5 g of 10% strength Pd/carbon at from 30 to 35° C. The catalyst is filtered off, the solution is evaporated down and the resulting solid is dried. 145 g of 3-amino-2-methylbenzyl alcohol (mp. 104°-108° C.) are obtained.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated down
  3. customthe resulting solid is dried

Sources & evidence

ORD record
ord-d2994a821b114a3db75fcccbfcb90029
Source dataset
uspto-grants-1993_10
Patent number
US05256666

Reaction notes

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