Acetic Acid → 3-Nitro-1-naphthoic acid

HRID 1696481Notes

Reaction equation

HRID 1696481 reaction equation
[CH:1]1[CH:10]=[C:9]2C([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[CH:6]3)[CH:2]=1)=O.[OH-].[Na+].CC(O)=O>O.Cl>[N+:16]([C:5]1[CH:6]=[C:7]([C:14]([OH:15])=[O:13])[C:8]2[C:3]([CH:4]=1)=[CH:2][CH:1]=[CH:10][CH:9]=2)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 18194Naphthalic anhydride, 3-nitro-

Product 1

HCID 2307723-Nitro-1-naphthoic acidYield 61.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-nitro-1,8-naphthalic anhydride (21.8 g, 89.7 mmol) in H2O (550 mL) containing 14.4 g of NaOH was added a solution of yellow HgO (25.1 g) in a mixture of H2O (75 mL) and glacial AcOH (25 mL). After reflux for 4 days, the reaction mixture was cooled and filtered to afford the mercurated product, which was then refluxed in 700 mL of 5N HCl for 3 h. The cream-colored precipitate was filtered, washed with cold H2O, dried, and recrystallized from hot glacial AcOH to yield 3-nitronaphthalene-1-carboxylic acid (12 g). 1H NMR (300 MHz, DMSO-d6): δ 13.7 (brs, 1H), 9.18 (s, 1H), 8.93 (d, J=8.4 Hz, 1H), 8.70 (s, 1H), 7.88 (t, J=7.8 Hz, 1H), 7.76 (t, J=6.9 Hz, 1H).

Workup

  1. additionwas added a solution of yellow HgO (25.1 g)
  2. temperatureAfter reflux for 4 days
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered
  5. customto afford the mercurated product, which
  6. filtrationThe cream-colored precipitate was filtered
  7. washwashed with cold H2O
  8. customdried
  9. customrecrystallized from hot glacial AcOH

Sources & evidence

ORD record
ord-3edd355bf0fc40aa86dd650f1e174b26
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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