Sodium Hydroxide → 6-(Methoxycarbonyl)naphthalene-2-carboxylic acid

HRID 585299

Reaction equation

HRID 585299 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17]C)=[O:16])[CH:11]=2)[CH:6]=1)=[O:4].[OH-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([OH:17])=[O:16])[CH:9]=[CH:8]2)=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 61225Dimethyl-2,6-naphthalenedicarboxylate

Product 1

HCID 33802176-(Methoxycarbonyl)naphthalene-2-carboxylic acidYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-naphthalenedicarboxylic acid dimethyl ester (26.0 g, 106 mmol) was dissolved in N,N-dimethylformamide (500 ml), and a 1N aqueous sodium hydroxide solution (106 ml) was added dropwise thereto at 100° C. over 30 minutes. After stirred for 3 hours, the solvent was distilled off under reduced pressure, water was added to the residue and the insolubles were filtered off. Concentrated hydrochloric acid (9 ml) was added to the filtrate, the precipitated crude product was filtered, washed with water, and recrystallized from hot methanol to obtain 6-(methoxycarbonyl)-2-naphthalenecarboxylic acid (14.6 g) as a white powder.

Workup

  1. distillationthe solvent was distilled off under reduced pressure, water
  2. additionwas added to the residue
  3. filtrationthe insolubles were filtered off
  4. additionConcentrated hydrochloric acid (9 ml) was added to the filtrate
  5. customthe precipitated crude product
  6. filtrationwas filtered
  7. washwashed with water
  8. customrecrystallized from hot methanol

Sources & evidence

ORD record
ord-594f51b670d0431d827b73fdd5c9eb82
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Linked notes

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