4-Ethoxybenzaldehyde → 3-(4-Ethoxycinnamoyl)-7-methoxycoumarin

HRID 25874

Reaction equation

HRID 25874 reaction equation
[C:1]([C:4]1[C:5](=[O:16])[O:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH3:15])[CH:8]=2)(=[O:3])[CH3:2].[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)[CH3:18]>N1CCCCC1.C(#N)C>[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH:2][C:1]([C:4]2[C:5](=[O:16])[O:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[C:9]([O:14][CH3:15])[CH:8]=3)=[O:3])=[CH:22][CH:21]=1)[CH3:18]

Participants

5

Reactant 2

HCID 248344-EthoxybenzaldehydeHCID 20544753-Acetyl-7-methoxycoumarin

Product 1

HCID 541146183-(4-Ethoxycinnamoyl)-7-methoxycoumarin

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2.18 g 3-acetyl-7-methoxycoumarin and 1.65 g p-ethoxybenzaldehyde in 100 ml alcohol was heated under reflux on a steam bath. Acetonitrile was added until solution was attained. Fifty drops of piperidine were added and the reaction mixture heated under reflux for 90 minutes. An additional fifty drops of piperidine were added and the solution was heated under reflux another hour. The product separated upon cooling and was washed with alcohol before being recrystallized from a mixture of alcohol and acetonitrile.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux on a steam bath
  3. temperaturethe reaction mixture heated
  4. temperatureunder reflux for 90 minutes
  5. temperaturethe solution was heated
  6. temperatureunder reflux another hour
  7. customThe product separated
  8. temperatureupon cooling
  9. washwas washed with alcohol
  10. custombefore being recrystallized from a mixture of alcohol and acetonitrile

Sources & evidence

ORD record
ord-943fff4c598841fc8e0531cb49187a38
Source dataset
uspto-grants-1979_04
Patent number
US04147552

Linked notes

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