Potassium Hydroxide → 2-(3-Methyl-4-nitrophenyl)acetic acid

HRID 494384Notes

Reaction equation

HRID 494384 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:23])[CH:7]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([CH3:22])[CH:14]=1)C(OCC)=O)C>CO.O>[CH3:22][C:15]1[CH:14]=[C:13]([CH2:7][C:6]([OH:23])=[O:5])[CH:18]=[CH:17][C:16]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 23130308Diethyl 2-(3-methyl-4-nitrophenyl)malonate

Product 1

HCID 107503542-(3-Methyl-4-nitrophenyl)acetic acidYield 86.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Potassium hydroxide (0.168 g) was dissolved in 7 mL of methanol and 1 mL of water, and the 2-(3-methyl-4-nitrophenyl)malonic acid diethyl ester (0.250 g) obtained in Example 1-3a) was dissolved in the solution. The solution was stirred at 100° C. for 2 hours and concentrated. The residue was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate and concentrated to give the title compound (0.143 g) as a yellow solid.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a047aa2ebac4aeb97dc9bc3efdce700
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Reaction notes

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