p-Anisoyl chloride → 2-(4-Methoxyphenyl)-3-methyl-8-(prop-1-en-1-yl)-4H-1-benzopyran-4-one

HRID 1981917Notes

Reaction equation

HRID 1981917 reaction equation
O[CH:2]([CH2:11]C=CC)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.CO[C:28]1[CH:36]=CC(C([O-])=O)=C[CH:29]=1.[Na+]>C(OCC)(=O)C>[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]2[O:22][C:6]3[C:5]([C:3](=[O:4])[C:2]=2[CH3:11])=[CH:10][CH:9]=[CH:8][C:7]=3[CH:29]=[CH:28][CH3:36])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 23663627Sodium anisate2×HCID 56606616HCID 56606616, compound

Product 1

HCID 541349382-(4-Methoxyphenyl)-3-methyl-8-(prop-1-en-1-yl)-4H-1-benzopyran-4-oneYield 75.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2.47 grams of 2-hydroxy-3-propenylpropiophenone are added 6.65 grams of p-methoxybenzoyl chloride and one half of 6.88 grams of anhydrous sodium p-methoxybenzoate, the mixture is heated in a nitrogen stream and, when 2-hydroxy-3-propenyl-propiopheone is dissolved, the residue of anhydrous sodium p-methoxybenzoate is added thereto, and the mixture is stirred at 180° to 190° C. for five hours. After cooled, the mixture is dissolved in ethyl acetate, the solution is washed with 10% sodium hydroxide solution and with water, and dried with anhydrous magnesium sulfate and finally the solvent is evaporated therefrom to give 3.0 grams of 4'-methoxy-3-methyl-8-propenylflavone, colorless needles, melting point 169° to 171° C.

Workup

  1. temperaturethe mixture is heated in a nitrogen stream and, when 2-hydroxy-3-propenyl-propiopheone
  2. dissolutionis dissolved
  3. temperatureAfter cooled
  4. washthe solution is washed with 10% sodium hydroxide solution and with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customfinally the solvent is evaporated

Sources & evidence

ORD record
ord-56a9e9b181304d3f8fd0e41256336480
Source dataset
uspto-grants-1986_06
Patent number
US04594345

Reaction notes

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