Acetic Acid → 2-(3-Methoxy-2-nitrophenyl)-4H-chromen-4-one

HRID 260086Notes

Reaction equation

HRID 260086 reaction equation
C(O)(=O)C.S(=O)(=O)(O)O.O[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[O:32])[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:22]=1[N+:29]([O-:31])=[O:30])=[O:20]>O>[CH3:28][O:27][C:23]1[C:22]([N+:29]([O-:31])=[O:30])=[C:21]([C:19]2[O:20][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17](=[O:32])[CH:18]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 224024981-(2-Hydroxyphenyl)-3-(3-methoxy-2-nitrophenyl)propane-1,3-dione

Product 1

HCID 224024972-(3-Methoxy-2-nitrophenyl)-4H-chromen-4-oneYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of glacial acetic acid (15 mL), concentrated sulfuric acid (180 mL), and 1-(2-hydroxy-phenyl)-3-(3-methoxy-2-nitrophenyl)propane -1,3 -dione (770 mg, 2.43 mmol) is heated at reflux for 2.5 hours. The hot solution is poured onto crushed ice and H2O (200 mL), stirring vigorously for 30 minutes. The solution is cooled in a refrigerator. The resulting solid is filtered and washed with H2O to yield 2-(3-methoxy-2-nitrophenyl)-4-oxo-4H-[1]benzopyran (510 mg, 70%) as a brown solid.

Workup

  1. temperatureat reflux for 2.5 hours
  2. additionThe hot solution is poured
  3. temperatureThe solution is cooled in a refrigerator
  4. filtrationThe resulting solid is filtered
  5. washwashed with H2O

Sources & evidence

ORD record
ord-9639366cc73c4670aed65e75b942fc59
Source dataset
uspto-grants-1996_06
Patent number
US05525625

Reaction notes

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