Sodium Acetate → 2-(3,4-dimethoxy-5-nitrophenyl)-4H-1-benzopyran-4-one

HRID 1781881Notes

Reaction equation

HRID 1781881 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([N+:23]([O-:25])=[O:24])[C:20]=1[O:21][CH3:22])[C:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[O:17])[CH3:16])=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15](=[O:17])[CH:16]=2)[CH:18]=[C:19]([N+:23]([O-:25])=[O:24])[C:20]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 21458954o-Acetylphenyl 3,4-dimethoxy-5-nitrobenzoate

Product 1

HCID 214591082-(3,4-dimethoxy-5-nitrophenyl)-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.0 g of o-acetylphenyl 3,4-dimethoxy-5-nitrobenzoate in 12.5 ml of glacial acetic acid is treated with 0.94 g of sodium acetate and held at the reflux temperature for 4 hours. After cooling the mixture is poured into ice-water. The separated crystals are filtered under suction. After recrystallization from ethyl acetate/hexane there is obtained 2-(3,4-dimethoxy-5-nitrophenyl)-4H-1-benzopyran-4-one in the form of colorless crystals of m.p. 216°-217°.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationThe separated crystals are filtered under suction
  3. customAfter recrystallization from ethyl acetate/hexane there

Sources & evidence

ORD record
ord-705ed834130c4adcb591f79eeb956aff
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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