Hydrochloric Acid → 5-Fluoro-6-hydroxynaphthalene-1-carboxylic acid

HRID 2115856Notes

Reaction equation

HRID 2115856 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:15]([O:17]C)=[O:16].Cl>O.CO>[F:3][C:4]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24823729Methyl 5-fluoro-6-hydroxynaphthalene-1-carboxylate

Product 1

HCID 248246045-Fluoro-6-hydroxynaphthalene-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydroxide (116 g, 2.9 mol) was dissolved in 100 mL water and added to a solution of methyl 5-fluoro-6-hydroxy-1-naphthoate (8.56 g, 38.9 mmol) in methanol (200 mL). The mixture was refluxed at 80° C. for 2 h. The mixture was allowed to cool to RT, then poured into 6N HCl in ice. The pH was adjusted to 3 to give a fine purple/pink solid. The title compound was isolated by centrifuge (with some salts).

Workup

  1. temperatureto cool to RT
  2. customto give a fine purple/pink solid

Sources & evidence

ORD record
ord-a66f1816767e4f3d92365d740a708d6d
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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