Toluene → 7-Hydroxy-2-methoxy-4H-1-benzopyran-4-one

HRID 601658Notes

Reaction equation

HRID 601658 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].C1(C)C=CC=CC=1.[CH3:12][O:13][C:14]1[O:15][C:16]2[C:21]([C:22](=[O:24])[CH:23]=1)=[CH:20][CH:19]=[C:18]([O:25]C)[CH:17]=2>O>[OH:25][C:18]1[CH:17]=[C:16]2[C:21]([C:22](=[O:24])[CH:23]=[C:14]([O:13][CH3:12])[O:15]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6451240Aluminum(III) ChlorideHCID 23158330HCID 23158330, compound

Product 1

HCID 231051467-Hydroxy-2-methoxy-4H-1-benzopyran-4-oneYield 64.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Under nitrogen atmosphere, 170 mg of aluminium trichloride was added to 5 ml solution of toluene with 103 mg of 2,7-dimethoxy-4H-chromen-4-one, and the mixture was stirred at 90° C. for 4 hours. Water was added to the reaction solution, the deposited white solid was filtered, separated and purified by preparative thin-layer chromatography (chloroform/methanol=9/1), to obtain 62 mg of the above compound as a white solid.

Workup

  1. filtrationthe deposited white solid was filtered
  2. customseparated
  3. custompurified by preparative thin-layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-5904dc82d1834df4910a2eb33b2bd1e1
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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