Sodium Hydroxide → HCID 178525987, compound

HRID 1004231Notes

Reaction equation

HRID 1004231 reaction equation
[OH:1][C:2](=[CH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)=[O:9])[C:3]([O:5]C)=[O:4].[OH-].[Na+]>C(O)C>[OH:1][C:2](=[CH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)=[O:9])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501818HCID 178501818, compound

Product 1

HCID 178525987HCID 178525987, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice cooled solution of Methyl 2-hydroxy-4-(3',4'-dichlorophenyl)-4-oxo-2-butenoate (1 g, 3.6 mmol) in 95% ethanol (120 mL), 1N sodium hydroxide (7.2 mL, 7.2 mmol) were added on stirring, the resulting mixture was stirred at 0° C. for 2 hours and at room temperature for further 3 hours. The most of solvent was removed under reduced pressure and the residue taken up with 2 N HCl, the resulting suspension was stirred for 5 minutes and then filtered. The solid was washed with water, dried and recrystallized from methanol to provide the pure acid as colourless prisms (845 mg, 90%), mp.180-181° C.

Workup

  1. stirringthe resulting mixture was stirred at 0° C. for 2 hours and at room temperature for further 3 hours
  2. customThe most of solvent was removed under reduced pressure
  3. stirringthe resulting suspension was stirred for 5 minutes
  4. filtrationfiltered
  5. washThe solid was washed with water
  6. customdried
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7867bc8ef8134f4088671e273db30734
Source dataset
uspto-grants-2000_04
Patent number
US06048896

Reaction notes

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