HCID 66701283, compound → HCID 66701165, compound

HRID 2075490Notes

Reaction equation

HRID 2075490 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([F:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:16]COC)=[O:4].O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>ClCCl>[F:15][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:16])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:14]=1

Participants

4

Reactant 2

HCID 66701283HCID 66701283, compoundHCID 71586775Bentonite

Product 1

HCID 66701165HCID 66701165, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.375 g of 4-fluoro-1-methoxymethoxynaphthalene-2-carboxylic acid methyl ester and 375 mg of montmorillonite K-10 clay was added 10 ml of dry dichloromethane. The mixture was stirred at room temperature for 35 minutes. The suspension was diluted with dry dichloromethane and filtered. The residue was washed with ethyl acetate and the combined filtrate concentrated to a white solid. The material was purified by flash chromatography on silica gel, eluting with ethyl acetate/heptanes to provide 0.191 g of 4-fluoro-1-hydroxynaphthalene-2-carboxylic acid, methyl ester.

Workup

  1. filtrationfiltered
  2. washThe residue was washed with ethyl acetate
  3. concentrationthe combined filtrate concentrated to a white solid
  4. customThe material was purified by flash chromatography on silica gel
  5. washeluting with ethyl acetate/heptanes

Sources & evidence

ORD record
ord-33afcb050f154cfc83e463611ef127f1
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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