2-(3-HYDROXY-3-METHYLBUTYL)PHENOL synthesis

11synthesis methods

Product Name:2-(3-HYDROXY-3-METHYLBUTYL)PHENOL
CAS Number:4167-73-1
Molecular formula:C11H16O2
Molecular Weight:180.24

676-58-4 Synthesis

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

119-84-6 Synthesis

119-84-6
430 suppliers
$5.00/5g

4167-73-1
22 suppliers
$115.00/1 G

Yield: 100%

Reaction Conditions:

in tetrahydrofuran at 0 - 20;

Steps:

2-(3-Hydroxy-3-methylbutyl)phenol (7)
To a solution of dihydrocoumarin (5.0 g, 33.75 mmol) in anhydrous THF (50 mL) at 0 °C was added dropwise methylmagnesium chloride (101.1 mmol, 33.7 mL, 3.0 M in THF). The reaction mixture was slowly warmed to room temperature and stirred overnight. On completion, the reaction mixture was treated with ice chips containing 25 mL of 1N H₂SO₄. Extraction of the aqueous phase with Et₂O, drying the latter over Na₂SO₄ and concentration under reduced pressure yielded the diol as a white solid (6.07 g, 100%): mp 110-112 °C; TLC R_f 0.37 (EtOAc : Hex, 1:1); ¹H NMR (600 MHz, (CD₃)₂CO) δ 8.22 (broad s, 1H), 7.06-7.07 (m, 1H), 6.97 (m, 1H), 6.77-6.79 (m, 1H), 6.72 (m, 1H), 3.54 (s, 1H), 2.67-2.70 (m, 2H), 1.71-1.73 (m, 2H), 1.22 (s, 6H); ¹³C NMR (400 MHz, (CD₃)₂CO) δ 155.2, 129.9, 129.6, 126.8, 119.6, 115.2, 69.7, 44.1, 29.2, 25.1. Anal. (%) calcd for C₁₁H₁₆O₂ C 73.30, H 8.95; found C 73.28, H 8.97.

References:

Jetson, Rachael;Malik, Neha;Luniwal, Amarjit;Chari, Venkatesh;Ratnam, Manohar;Erhardt, Paul [European Journal of Medicinal Chemistry,2013,vol. 63,p. 104 - 108] Location in patent:supporting information

496-16-2 Synthesis