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

HRID 1856950Notes

Reaction equation

HRID 1856950 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]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:15]=1C=O.Cl.O.[CH3:26]O>>[CH3:23][O:22][C:18]1[CH:15]=[C:14]([O:13][CH3:12])[CH:21]=[CH:20][C:19]=1[CH:26]=[C:7]1[C:6](=[O:9])[C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][C:4]=2[O:8]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 964042,6-DimethoxybenzaldehydeHCID 2357176-Hydroxy-3-coumaranone

Product 1

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

Procedure

After 6-hydroxy-2H-benzofuran-3-one 1 g and 2,6-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. After the solution was cooled to room temperature, water 400 ml was added. The 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. filtrationThe precipitated crystals were filtered
  3. dry with materialdried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-9c2f7ed87ccb4fba96bc0833f1383444
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

Loading…