ChemicalBook CAS DataBase List (3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol synthesis

5synthesis methods

Product Name:(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
CAS Number:443776-76-9
Molecular formula:C13H19BO3
Molecular Weight:234.1

3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE

380151-86-0

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

443776-76-9

GENERAL METHOD: Methanol (12.50 mL) was added to a mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol). The mixture was stirred at room temperature for 6 hours. Upon completion of the reaction, the crude reaction mixture was filtered and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Subsequently, the reaction mixture was stirred for another 5 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated in vacuum to afford the target product 3-hydroxymethylphenylboronic acid pinacol ester (2a) as a white solid (melting point 75-77 °C) in 88% yield (513 mg).1H-NMR (CD3OD-d4) δ ppm: 7.71 (d, J=8.0 Hz, 2H), 7.35 (d, J=7.8 Hz. 2H), 4.62 (s, 2H), 1.34 (s, 12H); 13C-NMR (CD3OD-d4) δppm: 146.23, 135.93, 127.26, 85.19, 65.24, 25.34; 11B-NMR (CDCl3) δppm: 34.82.

380151-86-0
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443776-76-9
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$8.00/250mg

Yield:443776-76-9 502 mg

Reaction Conditions:

with sodium tetrahydroborate at 20; for 5 h;

Steps:

[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (2a).
General procedure: To a mixture of a4-formylbenzenboronic acid (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol), methanol was added (12.50 mL). The mixture was stirred at room temperature for 6 h. After the reaction was completed, the crude solution was filtered, and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Afterwards, the reaction mixture was stirred for an additional 5 h. Once the reaction was completed, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give the desired product 2a as a white solid (m.p. 75-77 °C) in88% yield (513 mg). ¹H-NMR (CD₃OD-d₄) δ ppm 7.71 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 7.8 Hz, 2H),4.62 (s, 2H), 1.34 (s, 12H); ¹³C-NMR (CD₃OD-d₄) δ ppm 146.23, 135.93, 127.26, 85.19, 65.24, 25.34;¹¹B-NMR (CDCl₃) δ ppm 34.82.

References:

Chung, Sheng-Hsuan;Lin, Ting-Ju;Hu, Qian-Yu;Tsai, Chia-Hua;Pan, Po-Shen [Molecules,2013,vol. 18,# 10,p. 12346 - 12367]

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