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

HRID 1925362Notes

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

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

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

Sources & evidence

ORD record: ord-a1ef9a602ed64e72b2fa796ab2c0135e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178557B2

Reaction notes

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