Hydrochloric Acid → HCID 59326505, compound

HRID 238594Notes

Reaction equation

HRID 238594 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15]C(=O)C)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:19])[CH:11]=2)[CH:6]=1)=[O:4].C[O-].[Na+].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:19])[CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 593266124-Acetoxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 59326505HCID 59326505, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-acetoxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (1 g, 3.8 mmol) in methanol (20 mL) was added sodium methoxide (309 mg, 5.7 mmol). After being stirred at room temperature for 1 hour, the reaction mixture was acidified with 1 N hydrochloric acid to pH 3. The resulting precipitate was collected by filtration and dissolved in ethyl acetate. The organic solution was dried over sodium sulfate, and concentrated in vacuo to afford 900 mg of crude 6-fluoro-4-hydroxy-naphthalene-2-carboxylic acid methyl ester as a pale yellow solid, which was used in the next step without further purification.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialThe organic solution was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d47b1d7177043cd92e29110a7a58cf5
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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