Benzoyl chloride → HCID 19097459, compound

HRID 1197115Notes

Reaction equation

HRID 1197115 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:14]([O:7][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][C:1]([OH:13])=[O:12])[CH:11]=[CH:10][C:8]=1[O:9][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 348154Dihydrocaffeic acid

Product 1

HCID 19097459HCID 19097459, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3 g of dihydrocaffeic acid was dissolved in 20 ml of pyridine, and 5 g of benzoyl chloride was then gradually added thereto under cooling. After stirring at room temperature for 2 hours, the solvent was distilled off, and the resultant residue was then poured into 50 ml of ice water. This solution was neutralized with 6N hydrochloric acid and then extracted with 50 ml of chloroform twice. After washed with a saturated saline solution, the extracted material was dried over Glauber's salt, and the solvent was then distilled off under reduced pressure, thereby obtaining 6.8 g of 3-(3,4-dibenzoyloxyphenyl)propionic acid.

Workup

  1. temperatureunder cooling
  2. distillationthe solvent was distilled off
  3. additionthe resultant residue was then poured into 50 ml of ice water
  4. extractionextracted with 50 ml of chloroform twice
  5. washAfter washed with a saturated saline solution
  6. dry with materialthe extracted material was dried over Glauber's salt
  7. distillationthe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-00250016b654464c919088b01b619ae6
Source dataset
uspto-grants-1992_05
Patent number
US05116979

Reaction notes

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