4-Hydroxybenzaldehyde → 4-Hydroxybenzylamine

HRID 2079957Notes

Reaction equation

HRID 2079957 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH3:10]>CO.[Ni]>[NH2:10][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 222Ammonia

Product 1

HCID 974724-Hydroxybenzylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (10 g, 81.9 mmol) in methanol (45 mL) was added Raney nickel (3 g) and 7N aqueous ammonia solution (45 mL), and the solution was stirred under hydrogen atmosphere (1 atm) at room temperature for 21 hours. The reaction solution was filtered through Celite pad to remove the catalyst, the filtrate was concentrated, and 4-aminomethyl-phenol (10 g, quantitatively) was obtained as a pale green solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite pad
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-160243ba83134f7f83da664d6749a113
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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