Potassium Hydroxide → 2-(4-Chloro-3-nitrophenyl)-2-methylpropanoic acid

HRID 352385Notes

Reaction equation

HRID 352385 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22709425Methyl 2-(4-chloro-3-nitrophenyl)-2-methylpropionate

Product 1

HCID 227094342-(4-Chloro-3-nitrophenyl)-2-methylpropanoic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 200 ml of methanol was dissolved 75.5 g of methyl 2-(4-chloro-3-nitrophenyl)-2-methylpropionate. Under ice cooling, 70 ml of an aqueous solution of 49.3 g of potassium hydroxide was added dropwise and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added water and n-hexane to separate the mixture into layers. Concentrated hydrochloric acid was added to the aqueous layer to adjust its pH to 2 or less, followed by extraction with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to obtain 53.1 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue were added water and n-hexane
  3. customto separate the mixture into layers
  4. additionConcentrated hydrochloric acid was added to the aqueous layer
  5. extractionless, followed by extraction with ethyl acetate
  6. washThe ethyl acetate layer was washed successively with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-80ac47146f9549d1bc8a3906d643afe7
Source dataset
uspto-grants-2004_06
Patent number
US06747022B2

Reaction notes

Loading…