Sodium Hydroxide → 2-Benzyl-4-nitro-benzoic acid

HRID 496632Notes

Reaction equation

HRID 496632 reaction equation
[OH-].[Na+].C[C:4]1[C:5]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=[O:8]>CO>[CH2:16]([C:5]1[CH:4]=[C:12]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22321881HCID 22321881, compound

Product 1

HCID 223219062-Benzyl-4-nitro-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N Aqueous sodium hydroxide solution (2.0 mL, 4 mmol) was added to a solution of compound (28) (2.06 mmol) in methanol (10 mL) at ambient temperature. After 2 hrs the reaction mixture was evaporated to remove the methanol and then partitioned between ethyl ether (20 mL) and 2N aqueous sodium hydroxide solution (20 mL). The aqueous phase was acidified to pH⅔ with 2N HCl and extracted with ethyl acetate(3×20 mL). The combined organics were washed with water (20 mL) and brine (20 mL), filtered through phase separating paper and evaporated to yield 2-benzyl-4nitrobenzoic acid (compound 29).

Workup

  1. customAfter 2 hrs the reaction mixture was evaporated
  2. customto remove the methanol
  3. custompartitioned between ethyl ether (20 mL) and 2N aqueous sodium hydroxide solution (20 mL)
  4. extractionextracted with ethyl acetate(3×20 mL)
  5. washThe combined organics were washed with water (20 mL) and brine (20 mL)
  6. filtrationfiltered through phase
  7. customseparating paper
  8. customevaporated

Sources & evidence

ORD record
ord-62404d69730a4060a8d31770412df45f
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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