Hydrochloric Acid → HCID 20464764, compound

HRID 325417Notes

Reaction equation

HRID 325417 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][CH2:6][C:7]1[CH:8]=[C:9]([C:18](=[O:24])[C:19]([O:21]CC)=[O:20])[N:10]([CH3:17])[C:11]=1[C:12]([O:14]CC)=[O:13].[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][CH2:6][C:7]1[CH:8]=[C:9]([C:18](=[O:24])[C:19]([OH:21])=[O:20])[N:10]([CH3:17])[C:11]=1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20464708HCID 20464708, compound

Product 1

HCID 20464764HCID 20464764, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(m-chlorophenoxy)methyl-5-ethoxycarbonyl-1-methyl-α-oxopyrrole-2-acetate (7.96 g, 21 mmol) is placed in a 100 ml recovery flask and 25 ml 2.5 N aqueous sodium hydroxide (62.5 mmol) are added. The flask is heated with stirring under nitrogen to 74°. Ethanol (4 ml) is added and the solid begins to dissolve. After 15 minutes the reaction is homogeneous. After heating for one hour, the flask is cooled and 2.5 N aqueous HCl (30 ml, 75 mmol) is added slowly to precipitate the diacid. The resulting solid is filtered, washed with H2O, and then dried in vacuo to give 7.0 g of crude 4-(m-chlorophenoxy)methyl-5-hydroxycarbonyl-1-methyl-α-oxopyrrole-2-acetic acid.

Workup

  1. temperatureThe flask is heated
  2. dissolutionto dissolve
  3. temperatureAfter heating for one hour
  4. temperaturethe flask is cooled
  5. customto precipitate the diacid
  6. filtrationThe resulting solid is filtered
  7. washwashed with H2O
  8. customdried in vacuo

Sources & evidence

ORD record
ord-5b8e18391cc8441ead47c354be8eddd7
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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