Acetone → 6-Acetyl-4-oxo-4H-1-benzopyran-3-carbonitrile

HRID 2083230Notes

Reaction equation

HRID 2083230 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]=[C:10]([C:13]#[N:14])[C:9](=[O:15])[C:8]=2[CH:16]=1)[CH3:3].CC(C)=O.S(=O)(=O)(O)O>[O-2].[O-2].[O-2].[Cr+6].O>[C:2]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]=[C:10]([C:13]#[N:14])[C:9](=[O:15])[C:8]=2[CH:16]=1)(=[O:1])[CH3:3]

Participants

6

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 136013256-(1-Hydroxyethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile

Product 1

HCID 137286106-Acetyl-4-oxo-4H-1-benzopyran-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To a solution of 0.645 part of 6-(1-hydroxyethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile in 20 parts by volume of acetone under stirring at room temperature is added dropwise over a period of 1 hour 1.0 part by volume of a solution which is prepared from chromium trioxide, 97% sulfuric acid and water in a ratio of 6.0 parts: 3.6 parts by volume: 18 parts by volume. The dark-green resins precipitated in the flask bottom is separated from the reaction mixture by decantation, and the solution is concentrated at room temperature to a one-third volume and then admixed with water to give precipitates. The precipitates collected by filtration is washed with water and recrystallized from ethyl acetate. The procedure yields 0.440 part of 6-acetyl-4-oxo-4H-1-benzopyran-3-carbonitrile as colorless crystals. Melting point: 170°-172° C

Workup

  1. additionis added dropwise over a period of 1 hour 1.0 part by volume of a solution which
  2. customThe dark-green resins precipitated in the flask
  3. custombottom is separated from the reaction mixture by decantation
  4. concentrationthe solution is concentrated at room temperature to a one-third volume
  5. customto give
  6. customprecipitates
  7. filtrationThe precipitates collected by filtration
  8. washis washed with water
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-881a00b683aa4d73ae15280b2e2d8564
Source dataset
uspto-grants-1978_04
Patent number
US04085116

Reaction notes

Loading…