Hippuric Acid → 2-Carboxymethylbenzaldehyde hippuric acid

HRID 1020010Notes

Reaction equation

HRID 1020010 reaction equation
[C:1]([CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])([OH:3])=[O:2].[C:13]([OH:25])(=[O:24])[CH2:14][NH:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].C([O-])(=O)C.[K+].C(OC(=O)C)(=O)C>O>[C:13]([OH:25])(=[O:24])[CH2:14][NH:15][C:16]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:17].[C:1]([CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 464Hippuric AcidHCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 5289058Ortho-formylphenylacetic acid

Product 1

HCID 866643832-Carboxymethylbenzaldehyde hippuric acidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2-Carboxymethylbenzaldehyde (4.9 g, and 30 mmoles) with hippuric acid (5.9 g, 33 moles) and potassium acetate (2.94 g, 30 mmoles) were added to acetic anhydride (14.2 mls, 150 mmoles) and the reaction heated (100° C.) for 4 hours. To the cooled reaction was added water (100 mls) and stirred overnight. The resulting solid was collected by filtration and washed with water and dried (7.6 g, 83% yield).

Workup

  1. customTo the cooled reaction
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried (7.6 g, 83% yield)

Sources & evidence

ORD record
ord-4a4960fcc1c545198d1acb95e8f49687
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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