4-Hydroxybenzaldehyde → 4-Hydroxybenzylamine

HRID 1074425Notes

Reaction equation

HRID 1074425 reaction equation
[NH3:1].[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.S(=O)(=O)(O)O>[Ni].C(O)C>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:1])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 222AmmoniaHCID 1118Sulfuric Acid

Product 1

HCID 974724-Hydroxybenzylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Ammonia is passed into 500 ml of ethanol at 10° C. until saturation is reached, 122.1 g=1 mole of p-hydroxybenzaldehyde, 20 g of Raney nickel and 0.1 ml of concentrated sulfuric acid are added and the mixture is stirred in an autoclave for 6 hours at room temperature and under a hydrogen pressure of 100 atmospheres. After releasing the pressure, the catalyst is filtered off and the filtrate is boiled up with active charcoal, filtered and concentrated. The residue is recrystallized from a mixture of ethanol and ether. This gives 104 g (85% of theory), melting point: 104° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue is recrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-9a7203a6bd3644c2bf726f6e4e2ea594
Source dataset
uspto-grants-1983_07
Patent number
US04391805

Reaction notes

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