Benzoyl chloride → HCID 54459117, compound

HRID 1856934Notes

Reaction equation

HRID 1856934 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:13]=3[O:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([O:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:20][C:13]=3[O:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 54283810HCID 54283810, compound

Product 1

HCID 54459117HCID 54459117, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 2-[(3-methyl-4-methoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.5 g was dissolved in pyridine 5 ml, benzoyl chloride 0.282 ml was added, and the mixture was refluxed for 1.5 hours. The reaction mixture was cooled to room temperature, ethyl acetate 50 ml was added, and the mixture was washed with 2N-hydrochloric acid 50 ml and with saturated sodium bicarbonate solution 50 ml. The ethyl acetate solution was dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude extract was dissolved in hexane 10 ml and ethyl acetate 5 ml, and the precipitated crystals were filtered and dried over phosphorous pentoxide at a temperature of 60° C. for five hours under reduced pressure to obtain the desired compound 321.6 mg.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. washthe mixture was washed with 2N-hydrochloric acid 50 ml and with saturated sodium bicarbonate solution 50 ml
  3. concentrationconcentrated under reduced pressure
  4. extractionThe crude extract
  5. dissolutionwas dissolved in hexane 10 ml
  6. filtrationethyl acetate 5 ml, and the precipitated crystals were filtered
  7. dry with materialdried over phosphorous pentoxide at a temperature of 60° C. for five hours under reduced pressure

Sources & evidence

ORD record
ord-604831455bde408381bc5b9098b88067
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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