Methanol → 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-methyl-3-phenyl-

HRID 1862862Notes

Reaction equation

HRID 1862862 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([O:15]C(=O)C)[CH:12]=[C:11]2[C:6]=1[C:7](=[O:26])[C:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[C:9]([CH3:19])[O:10]2)(=O)C.CO.[OH-].[Na+].S(=O)(=O)(O)O>O>[OH:4][C:5]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]2[C:6]=1[C:7](=[O:26])[C:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[C:9]([CH3:19])[O:10]2

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 20394006HCID 20394006, compound

Product 1

HCID 53956954H-1-Benzopyran-4-one, 5,7-dihydroxy-2-methyl-3-phenyl-Yield 78.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g of 5,7-diacetoxy-2-methyl-isoflavone of m.p. 177°-178° C. prepared by the method described in Example 5 are boiled for 10 minutes with 50 ml of methanol and with a solution of 5 g of sodium hydroxide in 30 ml of water. On acidifying the solution with a 10% aqueous sulphuric acid, the precipitated product is filtered, affording 6 g of 5,7-dihydroxy-2-methyl-isoflavone, m.p. 228°-229° C.

Workup

  1. filtrationthe precipitated product is filtered

Sources & evidence

ORD record
ord-61610d850d794581b03bd6a423b6c053
Source dataset
uspto-grants-1979_09
Patent number
US04166862

Reaction notes

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