4-Hydroxy-3,5-dimethyl-benzaldehyde oxime → 4-(Aminomethyl)-2,6-dimethylphenol

HRID 844000Notes

Reaction equation

HRID 844000 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([CH:6]=[N:7]O)=[CH:4][C:3]=1[CH3:12]>C(O)(=O)C.[Zn]>[NH2:7][CH2:6][C:5]1[CH:4]=[C:3]([CH3:12])[C:2]([OH:1])=[C:10]([CH3:11])[CH:9]=1

Participants

4

Reactant 1

HCID 38748894-Hydroxy-3,5-dimethyl-benzaldehyde oxime

Product 1

HCID 136687374-(Aminomethyl)-2,6-dimethylphenolYield 98.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-Hydroxy-3,5-dimethyl-benzaldehyde oxime (1.0 grams, 6.06 mmole) in acetic acid (30 ml) and Zn dust (4.0 grams, 61.2 mmole) was stirred at ˜60° C. for 2 hours. The mixture was filtered through celite, basified by aqueous ammonium hydroxide and extracted with chloroform. The combined extracts were dried over MgSO4, filtered, and concentrated to give a foam (0.90 g). MW 151; MS (m/e) 151 (M+).

Workup

  1. filtrationThe mixture was filtered through celite
  2. extractionextracted with chloroform
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-12a5a383d806455398d54c6779301031
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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