Lithium Hydroxide → 3-Nitro-1-naphthoic acid

HRID 378124Notes

Reaction equation

HRID 378124 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O:16]C)=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[Li+].[OH-]>CO.O>[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 260948Methyl 3-nitronaphthalene-1-carboxylate

Product 1

HCID 2307723-Nitro-1-naphthoic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To methyl 3-nitro-1-naphthoate (2.5 g, 0.011 mole) (Aldrich) in MeOH/H2O (40 ml) (1:1) was added LiOH (1.8 g, 4 equivalents). The solution was stirred overnight at room temperature. The solvent was removed under a stream of N2. The residue was dissolved in H2O and the solution acidified with concentrated HCl. The resulting precipitate was filtered, washed with H2O and dried to yield 3-nitro-1-naphthoic acid (2.18 g) as a white solid.

Workup

  1. customThe solvent was removed under a stream of N2
  2. dissolutionThe residue was dissolved in H2O
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-1674374bd5754d5688a4db8ea468c333
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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