Benzoyl chloride → HCID 4555602, compound

HRID 1856936Notes

Reaction equation

HRID 1856936 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]2[C:14](=[O:15])[C:13]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:12]=3[O:11]2)=[CH:5][CH:4]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]2[C:14](=[O:15])[C:13]3[CH:16]=[CH:17][C:18]([O:20][C:21](=[O:28])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:19][C:12]=3[O:11]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 313110HCID 313110, compound

Product 1

HCID 4555602HCID 4555602, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 2-[(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 resulting crystals were dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 200.5 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. dry with materialThe resulting crystals were dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-6d3a3b7451f148289461b2299bf75dc1
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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