4-Hydroxybenzaldehyde → HCID 5153357, compound

HRID 1278443Notes

Reaction equation

HRID 1278443 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=O)=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(O)C>[C:24]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[C:9]2[C:10](=[O:11])[O:12][C:6]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:14][CH:13]=3)=[N:8]2)=[CH:18][CH:17]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7918Acetic AnhydrideHCID 260094-Chlorohippuric acid

Product 1

HCID 5153357HCID 5153357, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 60 g of N-(p-chlorobenzoyl)glycine, 34.5 g of p-hydroxybenzaldehyde, 23 g of fused sodium acetate and 170 ml of acetic anhydride was heated under reflux for 1 hour. The reaction mixture was cooled slightly and 400 ml of ethanol was added. A solid precipitated on cooling and was filtered and washed with cold ethanol and cold water. An analytical sample was made by recrystallization from CCL4 /EtOH/AcOH, m.p. 185-186.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction mixture was cooled slightly
  4. customA solid precipitated
  5. temperatureon cooling
  6. filtrationwas filtered
  7. washwashed with cold ethanol and cold water
  8. customAn analytical sample was made by recrystallization from CCL4 /EtOH/AcOH

Sources & evidence

ORD record
ord-0f40c5d96fce4f0196a0c700de6928aa
Source dataset
uspto-grants-1981_07
Patent number
US04281190

Reaction notes

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