Hydrochloric Acid → 2-[(2,4-Dimethoxyphenyl)methylidene]-6-hydroxy-2,3-dihydro-1-benzofuran-3-one

HRID 1856909Notes

Reaction equation

HRID 1856909 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[C:17]([CH:18]=O)=[CH:16][CH:15]=1.Cl.O>CO>[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[C:17]([CH:18]=[C:7]2[C:6](=[O:9])[C:5]3[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][C:4]=3[O:8]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 691752,4-DimethoxybenzaldehydeHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 37284202-[(2,4-Dimethoxyphenyl)methylidene]-6-hydroxy-2,3-dihydro-1-benzofuran-3-oneYield 47.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 6-hydroxy-2H-benzofuran-3-one 1 g and 4,6-dimethoxybenzaldehyde 1.23 g were dissolved in methanol 75 ml, concentrated hydrochloric acid 50 ml was added, and the mixture was refluxed for 1.5 hours. The solution was cooled to room temperature, water 400 ml was added, and precipitated crystals were filtered and dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 0.95 g.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. customprecipitated crystals
  3. filtrationwere filtered
  4. dry with materialdried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-425239cfedbd4e95a9afbd6c41a5f195
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

Loading…