Benzaldehyde → Benzoic acid, 4-[(phenylmethylene)amino]-, ethyl ester

HRID 1801235Notes

Reaction equation

HRID 1801235 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 2337Benzocaine

Product 1

HCID 96955Benzoic acid, 4-[(phenylmethylene)amino]-, ethyl esterYield 100.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-amino-benzoic acid ethyl ester (3.3 g, 20.0 mmol), benzaldehyde (2.4 g, 22.0 mmol) and p-toluenesulfonic acid (76 mg, 0.4 mmol) in toluene (60.0 mL) was heated to reflux for 12 h. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-(benzylidene-amino)-benzoic acid ethyl ester (5.1 g, quant.) as a light yellow solid: LC/MS m/e calcd for C16H15NO2 (M+H)+: 254.3, observed: 254.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-e6f13eac3af3497d83b687cf3fc3bce8
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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