Study On Synthesis Of 5-methyl-7-methoxy Isoflavone And Its Intermediate

The flavonoids is a useful chemistry material be paying attention widely, a lot of flavonoids be used as medcine to cure cardiopathy, osteoporosis and cough, be used as antioxidation for food, health food and animal feed additive . In this paper the synthesize method of isoflavone was introduced , 5-methyl-7-methoxyisoflavone and its intermediate 3, 5-dihydroxytoluene were studied in detail, and acquire the middle-experiment data via middle-experiment.As 3,5-dihydroxytoluene is a material, by Hoesch reaction(yield 55%), Frriedel-Crafts reaction (yield 25%), Neckis reaction (yield 40%) to get the intermediate 2, 4-dihydroxy-6-methyldeoxybenzoin respectively; 2, 4-dihydroxy-6-methyldeoxybenzoin by ethyl formate-sodium hydride cyclization (yield 93%), triethyl orthoformate-morpholine cyclization (yield 85%), boron trifluoride ether-DMF-methanesulfonyl chloride cyclization (yield 77%) to get 5-methyl-7-hydroxyisoflavone respectively, the 5-methyl-7-hydroxyisoflavone was identified by 'H NMR and MS, also synthesis 5-methyl-7-hydroxyisoflavone by combination-cyclization one-pot (total yield 46%); formation the 5-methyl-7-methoxy-isoflavone by NaOH solution methanation (yield 58%), K2CO3-acetone methanation (yield 57%)from 5-methyl-7-hydroxyisoflavone respectively. 5-methyl-7-methoxy-isof lavone single crystals was stuied by X-ray diffraction . The synthesis route made up of Hoesch reaction combination ethyl formate -sodium hydride cyclization NaOH solution methanation was done middle -experiment , the total yield of middle-experiment is 16. 8%.Synthesis 3, 5-dihydroxytoluene by ethyl acetoacetate and diketene as material ( yield 6%), by 3-methyl-4-chlorophenol and KOH as material (yield 30-40%) respectively, It was solved for product separation and purify. The synthesis route about 3-methyl-4-chlorophenol was done middle-experiment, the total yield of middle-experiment is 20%.