Benzoyl chloride → HCID 13335994, compound

HRID 979987Notes

Reaction equation

HRID 979987 reaction equation
C([O-])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[Cl:11][C:12]1[CH:22]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15]([OH:23])=[C:14]([C:24](=[O:27])[CH2:25][CH3:26])[CH:13]=1.[C:28](Cl)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:11][C:12]1[CH:13]=[C:14]2[C:15](=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:22]=1)[O:23][C:26]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[C:25]([CH3:28])[C:24]2=[O:27]

Participants

5

Reactant 4

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 517055Sodium BenzoateHCID 13478523HCID 13478523, compound

Product 1

HCID 13335994HCID 13335994, compoundYield 89.5%

Procedure

A 23.8 g (0.165 mole) quantity of sodium benzoate was added with stirring to a mixture of 12.8 g (0.05 mole) of ethyl 5-chloro-3-propionylsalicylate and 21.1 g (0.15 mole) of benzoyl chloride. The resulting mixture was heated at 180° to 190° C. for 8 hours to undergo reaction. The reaction mixture was cooled and 100 ml of a 5% aqueous solution of sodium carbonate was added. The mixture was stirred to precipitate solids. The solids were recrystallized from alcohol, giving 15.3 g (89.5%) of white crystals, M.P. 127.0° to 128.2° C. Table 1 below shows the results of chemical analysis.

Workup

  1. temperatureThe resulting mixture was heated at 180° to 190° C. for 8 hours
  2. customreaction
  3. temperatureThe reaction mixture was cooled
  4. customto precipitate solids
  5. customThe solids were recrystallized from alcohol

Sources & evidence

ORD record
ord-15c86818e33c4c53b063c316b0f309b8
Source dataset
uspto-grants-1987_01
Patent number
US04634768

Reaction notes

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