Method for preparing alcohol compound through uncatalyzed reaction of aromatic carboxylic acid
An aromatic carboxylic acid and alcohol compound technology, which is applied in the preparation of carboxylate, the preparation of organic compounds, and compounds containing elements of Group 3/13 of the periodic table, etc. High rate, wide application range, simple and controllable reaction process
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Embodiment 1
[0020] Embodiment one: pinacol borane and benzoic acid 3:1 mol ratio
[0021] Under an inert gas N2 atmosphere, add benzoic acid (61.1 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (218 μL, 1.5 mmol) with a pipette gun, and react at room temperature After 12 hours, the reaction was removed from the glove box, sampled, and NMR (with s-trimethoxybenzene (84.15 mg, 0.5 mmol) as the internal standard, dissolved in CDCl3, and stirred for 10 minutes), the calculated 1H yield was 99%, and the product NMR data: 1H NMR (400 MHz, CDCl3): δ 7.22– 7.32(m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3); add 1g to the sample residue Silica gel, using 3 mL of methanol as a solvent, reacted at 50 ° C for 3 h, further hydrolyzed the borate into alcohol, after the reaction, extracted three times with ethyl acetate, combined the organic layers, dried with anhydrous sodium sulfate, and removed the solvent under reduced pressure. Purificati...
Embodiment 2
[0022] Embodiment two: pinacol borane and benzoic acid 4:1 mol ratio
[0023] Under an inert gas N2 atmosphere, add benzoic acid (60.3 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (289 μL, 2 mmol) with a pipette gun, and react at room temperature After 6 hours, the reaction was removed from the glove box, and the reaction was completed to obtain boric acid ester, which was dissolved in CDCl3 with mes-trimethoxybenzene (83.05 mg, 0.5 mmol) as the internal standard, stirred for 10 minutes, sampled, and NMR. The 1H yield was calculated to be 90%. NMR data of the product: 1H NMR (400 MHz, CDCl3): δ 7.22– 7.32 (m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3). Add 1 g of silica gel to the sampling residue, use 3 mL of methanol as a solvent, and react at 50 ° C for 3 h to further hydrolyze the boric acid ester into alcohol. After the reaction, extract three times with ethyl acetate, combine the organic layers, and wash with...
Embodiment 3
[0024] Embodiment three: pinacol borane and benzoic acid 4:1 molar ratio
[0025] Under an inert gas N2 atmosphere, add benzoic acid (59.9 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (289 μL, 2 mmol) with a pipette gun, and react at room temperature After 12 hours, the reaction was removed from the glove box, and mes-trimethoxybenzene (82.50 mg, 0.5 mmol) was used as an internal standard, dissolved in CDCl3, stirred for 10 minutes, and sampled for NMR. The calculated 1H yield is 99%; NMR data of the product: 1H NMR (400 MHz, CDCl3): δ 7.22– 7.32 (m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3). Add 1 g of silica gel to the sampling residue, use 3 mL of methanol as a solvent, and react at 50 ° C for 3 h to further hydrolyze the boric acid ester into alcohol. After the reaction, extract three times with ethyl acetate, combine the organic layers, and wash with anhydrous sodium sulfate Dry, remove solvent under reduced...
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