Phenylacetic Acid → HCID 19741702, compound

HRID 2255116Notes

Reaction equation

HRID 2255116 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH:12]([NH:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18])[C:13]([OH:15])=[O:14]>CS(O)(=O)=O>[C:19]1([C:17]([NH:16][CH:12]([C:4]2[CH:5]=[CH:6][C:1]([CH2:7][C:8]([OH:10])=[O:9])=[CH:2][CH:3]=2)[C:13]([OH:15])=[O:14])=[O:18])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 999Phenylacetic AcidHCID 450272Alpha-Hydroxyhippuric acid

Product 1

HCID 19741702HCID 19741702, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of phenyl acetic acid (10.0 g, 73.5 mmol) in 25 ml methanesulfonic acid is treated with α-hydroxyhippuric acid (3.58 g, 18.4 mmol) and the resulting solution stirred at room temperature for 24 hours. The reaction mixture is poured onto ice (200 g) and the product extracted into ethyl acetate (3×200 ml). The combined organic layers are dried (Na2SO4) and concentrated. The residue is recrystallized from THF/diisopropyl ether. A tan solid which is α-[(phenylcarbonyl)amino]-1,4-benzenediacetic acid is obtained (1.5 g, 26%), mp 180°-220° C.

Workup

  1. additionThe reaction mixture is poured onto ice (200 g)
  2. extractionthe product extracted into ethyl acetate (3×200 ml)
  3. dry with materialThe combined organic layers are dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is recrystallized from THF/diisopropyl ether
  6. customis obtained (1.5 g, 26%), mp 180°-220° C.

Sources & evidence

ORD record
ord-775ea7ee53a94622922251254b2a90c6
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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