Sodium Hydroxide → HCID 19709581, compound

HRID 1247243Notes

Reaction equation

HRID 1247243 reaction equation
C[O:2][C:3](=[O:16])[CH:4]([O:14][CH3:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1.[OH-].[Na+]>O.CO>[CH3:15][O:14][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)[C:3]([OH:16])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20097113HCID 20097113, compound

Product 1

HCID 19709581HCID 19709581, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (RS)-methoxy-(3-nitro-phenyl)-acetic acid methyl ester (1.039 g) and NaOH (0.239 g) in water (0.75 ml) and methanol (10 ml) was stirred at 0° C. for 4.5 h. The reaction mixture was then concentrated (rotavapor, high vac.) and the residue (light yellow solid) was taken in water (25 ml). The resulting solution was acidified to pH˜1 by dropwise addition of 3.0 N HCl. This was extracted with EtOAc (50 ml+25 ml). The combined organics were dried (MgSO4), filtered and concentrated (rotavapor) to leave the crude (RS)-methoxy-(3-nitro-phenyl)-acetic acid (0.944 g) as a light yellow solid.

Workup

  1. concentrationThe reaction mixture was then concentrated (rotavapor, high vac.)
  2. additionThe resulting solution was acidified to pH˜1 by dropwise addition of 3.0 N HCl
  3. extractionThis was extracted with EtOAc (50 ml+25 ml)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated (rotavapor)

Sources & evidence

ORD record
ord-444c2345ecbc4eb6ac1ca998bbd12168
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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