Potassium Hydroxide → (3-Methoxy-4-nitrophenyl)acetic acid

HRID 2173402Notes

Reaction equation

HRID 2173402 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[OH-].[K+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 70559053HCID 70559053, compound

Product 1

HCID 16755859(3-Methoxy-4-nitrophenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of diethyl (3-methoxy-4-nitrophenyl)propanedioate (3.8 g, 12.219 mmol) in 30 mL of methanol and 20 mL of water was added KOH (2.05 g, 36.657 mmol) and the mixture was heated to 70° C. for 4 hours. Cooled to ambient temperature and removed the solvents under reduce pressure. The residue was added 100 mL of water and adjusted to pH=2 with conc. HCl. Extracted with EtOAc and the organic layer was washed with water, brine and dried over anhydrous sodium sulfate, concentrated to give (3-methoxy-4-nitrophenyl)acetic acid. 1H-NMR (400 MHz, MeOD) δ ppm 7.75 (d, J=8.6 Hz, 1H), 7.21 (d, J=1.6 Hz, 1H), 6.98 (dd, J=7.8 Hz, J=1.6 Hz, 1H), 3.93 (s, 3H), 3.70 (s, 2H).

Workup

  1. temperatureCooled to ambient temperature
  2. customremoved the solvents
  3. additionThe residue was added 100 mL of water
  4. extractionExtracted with EtOAc
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c57c72df9c6c459bb7557dc05447e053
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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