ChemicalBook CAS DataBase List 5-AMino-2,4-di-tert-butylphenol

5-AMino-2,4-di-tert-butylphenol synthesis

7synthesis methods

Product Name:5-AMino-2,4-di-tert-butylphenol
CAS Number:873055-58-4
Molecular formula:C14H23NO
Molecular Weight:221.34

To a refluxing solution of 2,4-di-tert-butyl-5-nitro-phenol (1.86 g, 7.40 mmol) and ammonium formate (1.86 g) in ethanol (75 mL) was added Pd-5% wt on activated carbon (900 mg). The reaction mixture was stirred at reflux for 2 h, cooled to room temperature, and filtered through Celite. The Celite was washed with methanol, and the combined filtrates were concentrated to yield 5-amino-2,4-di-tert-butyl-phenol as a grey solid (1.66 g, quant.).

873055-57-3 Synthesis

Phenol, 2,4-bis(1,1-diMethylethyl)-5-nitro-

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Yield:873055-58-4 100%

Reaction Conditions:

with ammonium formate;5%-palladium/activated carbon in ethanol for 2 h;Heating / reflux;

Steps:

5-Amino-2,4-di-tert-butyl-phenol
5-Amino-2,4-di-tert-butyl-phenol To a reluxing solution of 2,4-di-tert-butyl-5-nitro-phenol (1.86 g, 7.40 mmol) and ammonium formate (1.86 g) in ethanol (75 mL) was added Pd-5% wt. on activated carbon (900 mg). The reaction mixture was stirred at reflux for 2 h, cooled to room temperature and filtered through Celite. The Celite was washed with methanol and the combined filtrates were concentrated to yield 5-amino-2,4-di-tert-butyl-phenol as a grey solid (1.66 g, quant.). ¹H NMR (400 MHz, DMSO-d₆) δ 8.64 (s, 1H, OH), 6.84 (s, 1H), 6.08 (s, 1H), 4.39 (s, 2H, NH₂), 1.27 (m, 18H); HPLC ret. time 2.72 min, 10-99% CH₃CN, 5 min run; ESI-MS 222.4 m/z [M+H]⁺.

References:

VERTEX PHARMACEUTICALS INCORPORATED US2008/90864, 2008, A1 Location in patent:Page/Page column 8

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873055-57-3 Synthesis

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7440-44-0 Synthesis