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ChemicalBook CAS DataBase List (2-Chloro-5-methyl-phenyl)-methanol
89981-57-7

(2-Chloro-5-methyl-phenyl)-methanol synthesis

3synthesis methods
-

Yield:89981-57-7 390 mg

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0; for 0.333333 h;

Steps:

31.1 (1) Synthesis of 2-chloro-5-methylbenzyl alcohol [31-1] (hereinafter referred to as a compound [31-1])

(1) Synthesis of 2-chloro-5-methylbenzyl alcohol [31-1] (hereinafter referred to as a compound [31-1]) To a solution of 2-chloro-5-methylbenzoic acid (1.0 g) in tetrahydrofuran (59 mL) was added lithium aluminum hydride (445 mg) at 0°C, and the mixture was stirred at 0°C for 20 minutes. The reaction mixture was quenched with saturated aqueous solution of sodium sulfate, and the mixture was stirred at room temperature for 2 hours. The obtained white gel was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (390 mg) as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 7.29 (1H, s), 7.24 (1H, d, J = 8.4 Hz), 7.05 (1H, d, J = 7.6 Hz), 4.75 (2H, d, J = 6.3 Hz), 2.34 (3H, s), 1.91 (1H, t, J = 6.3 Hz).

References:

EP2878594,2015,A1 Location in patent:Paragraph 0499-0501