Sodium Hydroxide → HCID 18511494, compound

HRID 1819800Notes

Reaction equation

HRID 1819800 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([Cl:14])[CH:6]=1.[OH-].[Na+]>CO.O>[Cl:14][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:15])=[O:2])[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21129902Methyl 3-chloro-5-nitrobenzeneacetate

Product 1

HCID 18511494HCID 18511494, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (3-Chloro-5-nitro-phenyl)-acetic acid methyl ester (327, 920 mg, 4.0 mmol) in 20 mL of MeOH was added a solution of NaOH (EM, 1.6 g, 40 mmol) in 10 mL of H2O. The mixture was stirred for 2 h. MeOH was removed under reduced pressure, and the mixture was diluted with water, brought to pH 2 with con. HCl. The mixture was extracted 3× with EtOAc (50 mL). The organic layers were washed twice with a brine solution (50 mL), dried over Na2SO4. Removal of the solvent gave 810 mg (94%) of product. 1H NMR (400 MHz, DMSO-d6) δ 8.17-8.14 (m, 2H), 7.84 (br s, 1H), 3.77 (s, 3H).

Workup

  1. customMeOH was removed under reduced pressure
  2. additionthe mixture was diluted with water
  3. extractionThe mixture was extracted 3× with EtOAc (50 mL)
  4. washThe organic layers were washed twice with a brine solution (50 mL)
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-d9849878ba724c9782806982bde1c05c
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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