Sodium Hydroxide → 3-Methoxy-5-nitrobenzoic acid

HRID 266852Notes

Reaction equation

HRID 266852 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 877382Methyl 3-methoxy-5-nitrobenzoate

Product 1

HCID 53002123-Methoxy-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above ester (3.45 g, 16 mM) was dissolved in THF (100 ml), treated with 1M NaOH (25 ml), and stirred at ambient temperature for 5 hours. After removal of the solvent, the residue was treated with water (50 ml), acidified with 2M sulfuric acid, and extracted with ethyl acetate (3×60 ml). The combined organic extracts were washed with aqueous NaH2PO4, brine, and dried over MgSO4. Evaporation gave 3-methoxy-5-nitrobenzoic acid, which was allylated essentially as in Example 1, except that the chromatographic purification used a mixture of petrol/ethyl acetate (6:1), to give allyl 3-methoxy-5-nitrobenzoate. Nmr (CDCl3): δ 3.95 (s, 3H); 4.87 (dt, 2H); 5.31-5.48 (m, 2H); 5.95-6.15 (m, 1H); 7.89 (t, 1H); 7.92 (t, 1H); 8.46 (t, 1H).

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was treated with water (50 ml)
  3. extractionextracted with ethyl acetate (3×60 ml)
  4. washThe combined organic extracts were washed with aqueous NaH2PO4, brine
  5. dry with materialdried over MgSO4
  6. customEvaporation

Sources & evidence

ORD record
ord-4530c7c69b7e4a0a83879cdbcacbda99
Source dataset
uspto-grants-1997_07
Patent number
US05652233

Reaction notes

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