Benzoic Acid → HCID 13922249, compound

HRID 2413758Notes

Reaction equation

HRID 2413758 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:15]C(=O)CCC)(=O)[CH2:11][CH2:12][CH3:13].[N:21]1C=CC=C[CH:22]=1>>[C:1]([C:2]1[CH:7]=[CH:6][C:5]([CH2:22][NH:21][C:10](=[O:15])[CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1)([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 1049PyridineHCID 7798Butyric anhydride

Product 1

HCID 13922249HCID 13922249, compound

Procedure

4-Aminomethyl)benzoic acid (3.0 g) is suspended in pyridine (15 mL) and the mixture cooled in an ice water bath. Butyric anhydride (9.2 mL) is added dropwise to the stirred suspension over a 20 min period. The ice bath is removed and the mixture stirred at room temperature overnight. The mixture is poured into 150 mL ice water and made acidic (pH 1.5) by addition of concentrated HCl. The precipitate is recovered by suction filtration and recrystallized from ethyl acetate to produce N-(4-carboxybenzyl)butyramide, m.p. 186.5°-187.5° C.

Workup

  1. temperaturethe mixture cooled in an ice water bath
  2. customThe ice bath is removed
  3. additionThe mixture is poured into 150 mL ice water
  4. additionby addition of concentrated HCl
  5. filtrationThe precipitate is recovered by suction filtration
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f878977ca6d245b9b9fd2e7cbf9f4d7d
Source dataset
uspto-grants-1988_01
Patent number
US04719232

Reaction notes

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