2-METHYL-4-PHENYL-2-BUTANOL synthesis

6synthesis methods

Product Name:2-METHYL-4-PHENYL-2-BUTANOL
CAS Number:103-05-9
Molecular formula:C11H16O
Molecular Weight:164.24

By reaction of phenylethyl magnesium chloride with acetone

2550-26-7
352 suppliers
$9.00/100g

676-58-4 Synthesis

676-58-4
287 suppliers
$15.00/25ml

103-05-9
192 suppliers
$43.00/25g

Yield:103-05-9 72%

Reaction Conditions:

in tetrahydrofuran at 0; for 0.166667 h;Inert atmosphere;

Steps:

Synthesis of 2-methyl-4-phenylbutan-2-ol (25)
To a solution of S13 (1.00 mL, 6.68 mmol) in THF (33 mL) was added 3.0 M THF solution of MeMgCl (3.34 mL, 10.0 mmol) at 0 °C, and the mixture was stirred for 10 minutes. The reaction was quenched with saturated aqueous solution of NH4Cl, and the mixture was extracted with AcOEt (x3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (Hexane/AcOEt = 4/1) to give 25 (786 mg, 4.79 mmol, 72%) as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 7.34-7.20 (m, 5H), 2.71-2.67 (m, 2H), 1.80 (d, J = 17.4 Hz, 1H), 1.78-1.74 (m, 2H), 1.27 (s, 6H). This 1H NMR data is identical with that of ref 6.

References:

Tsutsumi, Tomohiro;Saitoh, Arisa;Kasai, Tomoyo;Chu, MengYue;Karanjit, Sangita;Nakayama, Atsushi;Namba, Kosuke [Tetrahedron Letters,2020,vol. 61,# 26,art. no. 152047] Location in patent:supporting information

558-30-5 Synthesis