3-Hydroxybenzaldehyde → 3(2H)-Benzofuranone, 6-hydroxy-2-[(3-hydroxyphenyl)methylene]-

HRID 1856906Notes

Reaction equation

HRID 1856906 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.[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.Cl.O>CO>[OH:12][C:13]1[CH:14]=[C:15]([CH:16]=[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:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 962WaterHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 4900593(2H)-Benzofuranone, 6-hydroxy-2-[(3-hydroxyphenyl)methylene]-Yield 70.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 6-hydroxy-2H-benzofuran-3-one 1 g and 3-hydroxybenzaldehyde 0.813 g were dissolved in methanol 75 ml, concentrated hydrochloric acid 50 ml was added, and the mixture was refluxed for two hours. The solution was cooled to room temperature, water 400 ml was added and allowed to stand for one hour. Precipitated crystals were filtered. The crystals were dried over phosphorous pentoxide at a temperature of 60° C. for five hours under reduced pressure to obtain the desired compound 1.20 g.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. customPrecipitated crystals
  3. filtrationwere filtered
  4. dry with materialThe crystals were dried over phosphorous pentoxide at a temperature of 60° C. for five hours under reduced pressure

Sources & evidence

ORD record
ord-1fd35ca8fae141c3a5cac3f5fd0cbf6d
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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