3-Methyl-4-nitrobenzyl alcohol → (4-amino-3-methylphenyl)methanol

HRID 1634076Notes

Reaction equation

HRID 1634076 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH2:5][OH:6]>C(O)C.[Pd]>[OH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([NH2:10])=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 1

HCID 5913603-Methyl-4-nitrobenzyl alcohol2×

Product 1

HCID 1514189(4-amino-3-methylphenyl)methanolYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-methyl-4-nitrobenzyl alcohol (compound 104, 8.5 g, 50.9 mmol) in ethanol (100 mL) was stirred at room temperature, while 10% Pd/C (1.0 g) was added in one portion. The resulting suspension was hydrogenated (10 psi) in a Parr apparatus at room temperature for 1.5 hours. The catalyst was removed by filtration, and solvent was evaporated under vacuum to give the title compound (105, 6.9 g, 99%). MS (electrospray) 138 (M+1); 1H N MR (CDCl3) δ 2.16 (s, 3H), 2.72 (br s, 3H), 4.52 (s, 2H), 6.64 (d, 1H, J=8.0 Hz), 7.02 (d, 1H, J=8.0 Hz), 7.05 (s, 1H).

Workup

  1. additionwas added in one portion
  2. customat room temperature
  3. customfor 1.5 hours
  4. customThe catalyst was removed by filtration, and solvent
  5. customwas evaporated under vacuum

Sources & evidence

ORD record
ord-a65176f0e1c84831a6d94cf0f442ed94
Source dataset
uspto-grants-2003_01
Patent number
US06506754B1

Reaction notes

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