Method for synthesizing 6-hydroxyl-1-anisindione
A synthesis method and technology of indanone are applied in a new synthesis field of 6-hydroxy-1-indanone, which can solve the problems of long route and difficulty in obtaining raw materials, and achieve the effects of simple processing, rapid preparation and easy amplification
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Embodiment 1
[0023] Synthesis of 1.3-chloropropionic acid phenol ester
[0024]
[0025] Phenol (5 g, 53 mmol) was dissolved in anhydrous dichloromethane (50 mL), triethylamine (5.35 g, 53 mmol) was added, and cooled to 0°C. Under nitrogen protection, acryloyl chloride (5.29 g, 58 mmol) was added dropwise, stirred at 0° C. for 1 hour, and at room temperature for 1 hour. The reaction solution was successively washed with water, washed with 1M NaOH, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and concentrated under reduced pressure to obtain phenol acrylate (6.7 g, yield 85%) 1 H NMR (CDCl 3 ): .6.03(d, 1H), 6.37(dd, 1H), 6.62(d, 1H), 7.16(m, 2H), 7.25(m, 1H), 7.41(m, 2H).
[0026] 2. Synthesis of 6-hydroxy-1-indanone
[0027]
[0028] Phenol acrylate (2 g, 13.5 mmol) was dissolved in trifluoromethanesulfonic acid (10.1 g, 67.6 mmol), and the reaction mixture was placed in an oil bath whose temperature had re...
Embodiment 2
[0030] Synthesis of 6-Hydroxy-1-indanone
[0031]
[0032] Phenyl acrylate (2 g, 13.5 mmol) was dissolved in trifluoromethanesulfonic acid (20.2 g, 135 mmol), and the reaction mixture was placed in an oil bath whose temperature had reached 170° C. under nitrogen protection, and stirred for 1 h. The reactant was cooled to room temperature, poured into 20 mL of ice water, extracted with dichloromethane (30 mL×3), combined the organic phases, washed with saturated sodium bicarbonate, water and saturated brine, dried over anhydrous sodium sulfate, and filtered to remove the desiccant. Concentrate under reduced pressure, and separate by silica gel column chromatography (PE / EA=4 / 1~2 / 1) to obtain 6-hydroxy-1-indanone (760 mg, yield 38%). 1 H NMR (CDCl 3 ): 2.71 (m, 2H), 3.05 (t, 2H), 5.99 (s, 1H), 7.14 (d, 1H), 7.21 (s, 1H), 7.33 (d, 1H).
Embodiment 3
[0034] Synthesis of 6-Hydroxy-1-indanone
[0035]
[0036] Phenyl acrylate (2 g, 13.5 mmol) was dissolved in trifluoromethanesulfonic acid (40.4 g, 270 mmol), and the reaction mixture was placed in an oil bath whose temperature had reached 170° C. under nitrogen protection, and stirred for 1 h. The reactant was cooled to room temperature, poured into 20 mL of ice water, extracted with dichloromethane (40 mL×3), combined the organic phases, washed with saturated sodium bicarbonate, water and saturated brine, dried over anhydrous sodium sulfate, and filtered to remove the desiccant , concentrated under reduced pressure, and separated by silica gel column chromatography (PE / EA=4 / 1~2 / 1) to obtain 6-hydroxy-1-indanone (700 mg, yield 35%). 1 H NMR (CDCl 3 ): 2.71 (m, 2H), 3.05 (t, 2H), 5.99 (s, 1H), 7.14 (d, 1H), 7.21 (s, 1H), 7.33 (d, 1H).
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