Phenylacetyl chloride → 7,8-Dimethoxy-6-nitro-3-phenyl-chromen-2-one

HRID 965777Notes

Reaction equation

HRID 965777 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:16])=[C:5]([CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[CH:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](Cl)=[O:25])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:12][O:11][C:10]1[C:3]([O:2][CH3:1])=[C:4]2[C:5]([CH:6]=[C:23]([C:20]3[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=3)[C:24](=[O:25])[O:16]2)=[CH:8][C:9]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 11430Potassium CarbonateHCID 223134323,4-Dimethoxy-2-hydroxy-5-nitrobenzaldehyde2×

Product 1

HCID 223134437,8-Dimethoxy-6-nitro-3-phenyl-chromen-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,4-dimethoxy-2-hydroxy-5-nitrobenzaldehyde obtained from Preparation example (1a) (0.91 g), phenacetylchloride (1.1 ml) and potassium carbonate (2.0 g) was refluxed in dry acetone (40 ml) overnight. Acetone was evaporated, cold water added and filtered. Yield: 0.69 g.

Workup

  1. customAcetone was evaporated
  2. additioncold water added
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ac5eef07ca214db78624677c1de3aea9
Source dataset
uspto-grants-2005_10
Patent number
US06951870B2

Reaction notes

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