Formaldehyde → 2,4-di-tert-butyl-6-(N-methylamino)phenol

HRID 2189626Notes

Reaction equation

HRID 2189626 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([NH2:15])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[BH3-][C:18]#N.[Na+].C=O>CO>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([NH:15][CH3:18])[C:6]=1[OH:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 3245552-Amino-4,6-di-tert-butylphenolHCID 5003444Sodium cyanoborohydride

Product 1

HCID 574702492,4-di-tert-butyl-6-(N-methylamino)phenolYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,4-di-tert-butyl-6-amino-phenol (C-9) (5.08 g, 23 mmol), NaBH3CN (4.41 g, 70 mmol) and paraformaldehyde (2.1 g, 70 mmol) in methanol (50 mL) was stirred at reflux for 3 h. After removal of the solvent, the residue was purified by column chromatography (petroleum ether-EtOAc, 30:1) to give 2,4-di-tert-butyl-6-(N-methylamino)phenol (C-24) (800 mg, 15%). 1H NMR (DMSO-d6) δ 8.67 (s, 1H), 6.84 (s, 1H), 5.99 (s, 1H), 4.36 (q, J=4.8 Hz, 1H), 2.65 (d, J=4.8 Hz, 3H), 1.23 (s, 18H); ESI-MS 236.2 m/z (MH+).

Workup

  1. temperatureat reflux for 3 h
  2. customAfter removal of the solvent
  3. customthe residue was purified by column chromatography (petroleum ether-EtOAc, 30:1)

Sources & evidence

ORD record
ord-e76a26c491604ef8b7ff76137fcbbf3b
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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