2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4H-1-Benzopyran-4-one, 2-(4-chlorophenyl)-7-methoxy-

HRID 2301343Notes

Reaction equation

HRID 2301343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][C:12]([O:19][CH3:20])=[CH:13][CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:15]([C:16](=[O:18])[CH:17]=2)=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 5270544HCID 5270544, compound

Product 1

HCID 4933754H-1-Benzopyran-4-one, 2-(4-chlorophenyl)-7-methoxy-Yield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

50 mg (0.17 mmol) of 2-(4-chloro-phenyl)-7-methoxy-chroman-4-one synthesized in Preparation 4 and 3.0 molar equivalents (0.12 g, 0.51 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was refuxed in benzene solvent for a day, and then benzene was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethylacetate=5/1, v/v) to give the title compound in a yield of 79%.

Workup

  1. custombenzene was removed by distillation under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-bb06ead2831640c48b6498aeaf00be15
Source dataset
uspto-grants-2002_12
Patent number
US06500846B1

Reaction notes

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