Ethyl Acetoacetate → 3-Acetyl-7-methoxycoumarin

HRID 25873

Reaction equation

HRID 25873 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:12](OCC)(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15]>N1CCCCC1>[C:14]([C:13]1[C:12](=[O:17])[O:1][C:2]2[C:3]([CH:4]=1)=[CH:6][CH:7]=[C:8]([O:10][CH3:11])[CH:9]=2)(=[O:15])[CH3:16]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 20544753-Acetyl-7-methoxycoumarin

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

A mixture of 15.2 g 2-hydroxy-4-methoxybenzaldehyde and 13.5 g ethyl acetoacetate was warmed on a hot plate until solution was attained. Thirty drops of piperidine were added and the reaction mixture continued to be heated gently. After several minutes the reaction mixture solidified. After cooling, the product was recrystallized from a mixture of alcohol and acetonitrile. Yield 20 g.

Workup

  1. temperaturewas warmed on a hot plate until solution
  2. temperatureto be heated gently
  3. waitAfter several minutes the reaction mixture solidified
  4. temperatureAfter cooling
  5. customthe product was recrystallized from a mixture of alcohol and acetonitrile

Sources & evidence

ORD record
ord-0dc7f5bd4b6b41e582a9b7b4128509d7
Source dataset
uspto-grants-1979_04
Patent number
US04147552

Linked notes

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