Ether bond dissociation method of phenylalkyl ether
A technology of phenyl alkyl ether and ether bond, which is applied in the field of intermediate synthesis of pharmaceuticals and chemical raw materials, and can solve the problem of severe exothermic reaction between iodine and aluminum powder, high price of aluminum triiodide, difficulty in using aluminum triiodide, etc. problems, to achieve the effect of low price, wide application range and easy operation
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Embodiment 1
[0027] Embodiment 1 (eugenol demethylation)
[0028]
[0029] Acetonitrile (40ml) was added to a 100ml round bottom flask, followed by aluminum trichloride (0.759g, 5.7mmol, 1.1eq), potassium iodide (0.948g, 5.7mmol, 1.1eq), DIC (0.378g, 2.9mmol, 0.6eq) and eugenol (0.844g, 5.1mmol), heated to 80°C, stopped stirring after 18 hours of reaction, cooled to room temperature, added 2mol / L dilute hydrochloric acid (10ml) into the round bottom flask for acidification, and dilute with ethyl acetate Esters (50ml×3) were extracted, the organic phases were combined, washed with a saturated aqueous solution of sodium thiosulfate (10ml), then washed with saturated brine (10ml), dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to dryness with a rotary evaporator , the residue was purified by flash column chromatography (eluent is petroleum ether / ethyl acetate=4:1, volume ratio) to obtain 0.504g 4-allyl catechol (off-white waxy solid, yield 65%).
[0030...
Embodiment 2
[0032] Embodiment 2 (eugenol demethylation)
[0033]
[0034] Acetonitrile (40ml) was added to a 100ml round bottom flask, followed by aluminum trichloride (0.738g, 5.5mmol, 1.1eq), sodium iodide (0.828g, 5.5mmol, 1.1eq), DIC (0.377g, 2.9 mmol, 0.6eq) and eugenol (0.824g, 5.0mmol), heated to 80°C, stopped stirring after 18 hours of reaction, and added 2mol / L dilute hydrochloric acid (10ml) to the round-bottomed flask to acidify after cooling to room temperature. Extract with ethyl acetate (50ml×3), combine the organic phases, wash with a saturated aqueous solution of sodium thiosulfate (10ml), then wash with saturated brine (10ml), dry over anhydrous magnesium sulfate, filter, and use a rotary evaporator for the filtrate Evaporated to dryness, the residue was purified by flash column chromatography (eluent: petroleum ether / ethyl acetate=4:1, volume ratio) to obtain 0.418g of 4-allyl catechol (off-white waxy solid, Yield 55%).
[0035] R f =0.44 (petroleum ether / ethyl ace...
Embodiment 3
[0036] Embodiment 3 (eugenol demethylation)
[0037]Acetonitrile (40ml) was added to a 100ml round bottom flask, followed by aluminum trichloride (0.770g, 5.7mmol, 1.1eq), potassium iodide (1.742g, 10.4mmol, 2eq), DIC (0.393g, 3.1mmol, 0.6 eq) and eugenol (0.863g, 5.2mmol), heated to 80°C, stopped stirring after 18 hours of reaction, cooled to room temperature, added 2mol / L dilute hydrochloric acid (10ml) to the round bottom flask for acidification, and used ethyl acetate (50ml×3) extraction, combined organic phases, first washed with saturated aqueous sodium thiosulfate (10ml), then washed with saturated brine (10ml), dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to dryness with a rotary evaporator, The residue was purified by flash column chromatography (eluent: petroleum ether / ethyl acetate=4:1, volume ratio) to obtain 0.643g of 4-allyl catechol (off-white waxy solid, yield 81 %).
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