2'-Hydroxyacetophenone → 3-Formylchromone

HRID 26658

Reaction equation

HRID 26658 reaction equation
[C:1](=[O:3])=O.[CH3:4]C(C)=O.[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[O:17])[CH3:16]>CN(C)C=O>[O:17]=[C:15]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH:4]=[C:16]1[CH:1]=[O:3]

Participants

4

Reactant 2

HCID 83752'-HydroxyacetophenoneHCID 18522661Acetone cardice

Product 1

HCID 871123-Formylchromone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 80 volume parts of dimethylformamide are dissolved 25 parts of orthohydroxyacetophenone and, while the solution is externally cooled to about -20° C. with dry ice-acetone, 80 volume parts of tetrachloropyrophosphoric acid are added dropwise to the solution. The resulting mixture is stirred at room temperature for 13 hours. Then, the reaction mixture is poured into ice water and the resulting crystals are recovered by filtration, washed with water and ethanol and finally recrystallized from acetone. The procedure yields of 4-oxo-4H-1-benzopyran-3-carboxaldehyde as colorless crystals melting at 152°-153° C.

Workup

  1. additionare added dropwise to the solution
  2. filtrationthe resulting crystals are recovered by filtration
  3. washwashed with water and ethanol
  4. customfinally recrystallized from acetone

Sources & evidence

ORD record
ord-96922e08165340108b55feb1592c051d
Source dataset
uspto-grants-1979_04
Patent number
US04151180

Linked notes

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