HCID 19741709, compound → p-Phenylenediacetic acid

HRID 2255117Notes

Reaction equation

HRID 2255117 reaction equation
C1(C(N[CH:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24]C)=[O:23])=[CH:17][CH:16]=2)[C:11]([O:13]C)=[O:12])=O)C=CC=CC=1>Cl>[C:18]1([CH2:21][C:22]([OH:24])=[O:23])[CH:17]=[CH:16][C:15]([CH2:10][C:11]([OH:13])=[O:12])=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 19741709HCID 19741709, compound

Product 1

HCID 81760p-Phenylenediacetic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of dimethyl α-[(phenylcarbonyl)amino]-1,4-benzenediacetate (1.00 g, 2.90 mmol) from the Preparation 2 above in 20 ml of 6N HCl is heated at reflux under N2 for 19 hours. The reaction mixture is cooled and extracted with a 1:1 toluene/ether solution (2×40 ml). The aqueous layer is concentrated and the residue dissolved in H2O (10 ml) and freeze-dried. A solid, 1,4-benzenediacetic acid, a-amino-, (±) is obtained (0.72 g, 76%), mp 205° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux under N2 for 19 hours
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with a 1:1 toluene/ether solution (2×40 ml)
  5. concentrationThe aqueous layer is concentrated
  6. dissolutionthe residue dissolved in H2O (10 ml)
  7. customfreeze-dried

Sources & evidence

ORD record
ord-d089fdc6f5754c44a0d1072e19b2cbd6
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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