Potassium Hydroxide → 5-Amino-2-methylphenol

HRID 1111509Notes

Reaction equation

HRID 1111509 reaction equation
C([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:12]N(C)C)=[C:9]([OH:11])[CH:10]=1)(=O)C.[OH-].[K+]>[Pd]>[NH2:4][C:5]1[CH:10]=[C:9]([OH:11])[C:8]([CH3:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11735930HCID 11735930, compound

Product 1

HCID 178185-Amino-2-methylphenolYield 68.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In the hydrogenolysis step, 8.0 g (38 mmol) of 5-acetamido-2-[(N,N-dimethylamino)methyl]phenol was dissolved in 54 ml (162 mmol) of 3N potassium hydroxide solution in a Parr bottle. Palladium on activated carbon (0.8 g; 3% Pd/C) was added to the solution. The reaction mixture was shaken under hydrogen on a Parr apparatus for 3 hours at 70°-80° C. and 60 psi. The catalyst (Pd/C) was removed by filtration and the filtrate brought to about pH 12 with 6M HC1 (15-20 ml). The off-white crystalline product precipitated out of solution. The solution was cooled and the precipitate filtered, washed with water, and dried overnight in a vacuum oven to give 3.2 g (68% yield) of 5-amino-o-cresol, m.p. 158°-160° C.). The purity of 5-amino-o-cresol prepared by this procedure was determined to be 97% by perchloric acid titration.

Workup

  1. customThe catalyst (Pd/C) was removed by filtration
  2. customThe off-white crystalline product precipitated out of solution
  3. temperatureThe solution was cooled
  4. filtrationthe precipitate filtered
  5. washwashed with water
  6. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-64413250e6bc4330ae84e5a811b35d15
Source dataset
uspto-grants-1990_12
Patent number
US04980505

Reaction notes

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