Acetic Acid → Ethyl 6,7-methylenedioxy-2-oxo-1-benzopyran-3-carboxylate

HRID 861878Notes

Reaction equation

HRID 861878 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]2[O:10][CH2:11][O:12][C:7]2=[CH:6][C:3]=1[CH:4]=O.[C:13](OCC)(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].N1CCCCC1.C(O)(=O)C>C(O)C>[CH2:11]1[O:10][C:8]2=[CH:9][C:2]3[O:1][C:13](=[O:20])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][C:3]=3[CH:6]=[C:7]2[O:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 67106266-Hydroxy-1,3-dioxaindane-5-carbaldehyde

Product 1

HCID 13193685Ethyl 6,7-methylenedioxy-2-oxo-1-benzopyran-3-carboxylateYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-hydoxy-4,5-methylenedioxybenzaldehyde (1.16 g), diethyl malonate (1.34 g), piperidine (0.3 g), acetic acid (0.035 ml) and ethanol (30 ml) was refluxed for 4 hours. After the reaction mixture was cooled, the resulting crystal was collected by filtration to yield ethyl 6,7-methylenedioxy-2-oxo-1-benzopyran-3-carboxylate (1.29 g, 70%) having a melting point of 200°-201° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter the reaction mixture was cooled
  3. filtrationthe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-378f57f3f5e54944ab41fea8bd7f3a72
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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