2'-Hydroxyacetophenone → 3-Formylchromone

HRID 1287311Notes

Reaction equation

HRID 1287311 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]>>[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

3

Reactant 2

HCID 83752'-HydroxyacetophenoneHCID 18522661Acetone cardice

Product 1

HCID 871123-Formylchromone

Procedure

In 80 volume parts of diemthylformamide there is dissolved 25 parts of orthohydroxyacetophenone and while the solution is externally cooled to about -20°C with dry ice-acetone, 80 volume parts of tetrachloropyrophosphate is added in small installments. The mixture is stirred at room temperature for 13 hours. The reaction mixture is then poured into ice-water and the resulting crystals are recovered by filtration, washed with water and ethanol and finally recrystallized from acetone. There is obtained a 19.6 parts yield of 4-oxo-4H-1-benzopyran-3-carboxaldehyde, as colorless crystals, melting at 152°-153°C.

Workup

  1. additionis added in small installments
  2. filtrationthe resulting crystals are recovered by filtration
  3. washwashed with water and ethanol
  4. customfinally recrystallized from acetone

Sources & evidence

ORD record
ord-f0a4136b7341424fa91412a1e15f60d6
Source dataset
uspto-grants-1976_10
Patent number
US03984441

Reaction notes

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