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Ethyl benzoylacetate → 3-Benzoyl-5,7-dimethoxy-2H-1-benzopyran-2-one

HRID 25872
Notes
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Reaction equation

HRID 25872 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](O)C(=[C:9]([O:11][CH3:12])[CH:10]=1)C=O.[C:14]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1CCCCC1.C(#N)C>[C:14]([C:22]1[C:23](=[O:24])[O:25][C:26]2[C:4]([CH:5]=1)=[C:3]([O:2][CH3:1])[CH:10]=[C:9]([O:11][CH3:12])[CH:27]=2)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 697254,6-Dimethoxysalicylaldehyde

Product 1

HCID 127770753-Benzoyl-5,7-dimethoxy-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 18.2 g 4,6-dimethoxysalicylaldehyde, 20.0 g ethyl benzoylacetate, 20 ml acetonitrile and 30 drops piperidine was heated gently on a hot plate for 45 minutes. After cooling the product was collected and recrystallized twice from acetonitrile and once from benzene containing a small amount of acetonitrile. m.p. 178° C.-179° C.

Workup

  1. temperaturewas heated gently on a hot plate for 45 minutes
  2. temperatureAfter cooling the product
  3. customwas collected
  4. customrecrystallized twice from acetonitrile and once from benzene containing a small amount of acetonitrile

Sources & evidence

ORD record
ord-ebb76a967e5e457da245dada4c59a35b
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04147552

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes