Hydrochloric Acid → (3-Ethyl-6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

HRID 238648Notes

Reaction equation

HRID 238648 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:14]([CH2:15][CH3:16])=[C:13]([O:17]C(=O)C)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=2)[CH:6]=1.C[O-].[Na+].Cl>CO>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:14]([CH2:15][CH3:16])=[C:13]([OH:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 59326550(4-Acetoxy-3-ethyl-6-fluoro-naphthalen-2-yl)acetic acid methyl ester

Product 1

HCID 59326490(3-Ethyl-6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl esterYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (4-acetoxy-3-ethyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (50 mg, 0.164 mmol), sodium methoxide (13 mg, 0.247 mmol), and methanol (4 mL) was stirred at room temperature for 2 hours. After the reaction mixture was acidified with concentrated hydrochloric acid to pH 5, a precipitate formed, which was then collected by filtration, and dissolved in ethyl acetate (20 mL). The organic solution was dried over sodium sulfate, and concentrated in vacuo to afford the crude product of (3-ethyl-6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (42 mg, 97.7%) as a light yellow solid.

Workup

  1. customa precipitate formed
  2. filtrationwhich was then collected by filtration
  3. dissolutiondissolved in ethyl acetate (20 mL)
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68472c4992bc455aa287b92fbbf72277
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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