ChemicalBook CAS DataBase List 1-(3,5-di-tert-butylphenyl)ethanone

1-(3,5-di-tert-butylphenyl)ethanone synthesis

13synthesis methods

Product Name:1-(3,5-di-tert-butylphenyl)ethanone
CAS Number:1756-31-6
Molecular formula:C16H24O
Molecular Weight:232.36

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Yield: 85%

Reaction Conditions:

in tetrahydrofuran;diethyl ether at -78 - 20;

Steps:

5.1.1. 1-(3,5-Di-tert-butylphenyl)ethanone (15)
1.6 N MeLi in Et₂O (300 μL, 0.480 mmol) was added to a solution of 14 (50.7 mg, 0.0216 mmol) in THF (1.0 mL) at -78 °C. The mixture was stirred at room temperature for 5 h, then poured into water and extracted with AcOEt. The organic layer was washed with brine and dried over MgSO₄. Filtration, evaporation of the solvent in vacuo and purification by flash column chromatography (AcOEt/n-hexane = 1/25) gave 42.5 mg (85%) of 15 as a yellow oil; ¹H NMR (CDCl₃, 500 MHz, δ; ppm) 7.81 (2H, d, J = 1.8 Hz), 7.65 (1H, t, J = 1.8 Hz), 2.63 (3H, s), 1.36 (18H, s); MS (FAB) m/z: 233 (MH⁺).

References:

Itoh, Yukihiro;Kitaguchi, Risa;Ishikawa, Minoru;Naito, Mikihiko;Hashimoto, Yuichi [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 22,p. 6768 - 6778] Location in patent:experimental part

22385-77-9 Synthesis