Hydrochloric Acid → Methyl 4-fluoro-2-(methoxymethoxy)benzoate

HRID 881588Notes

Reaction equation

HRID 881588 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[H-].[Na+].Cl[CH2:15][O:16][CH3:17].Cl.[CH3:19]N(C)C=O>>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[O:11][CH2:15][O:16][CH3:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 676614-Fluorosalicylic acid

Product 1

HCID 58437341Methyl 4-fluoro-2-(methoxymethoxy)benzoate

Procedure

To a solution of 4-fluoro-2-hydroxybenzoic acid (3.0 g) in N,N-dimethylformamide (5 mL) were added sodium hydride (60% 1.0 g) and (chloromethyl)methyl ether (2.1 g) at room temperature, and this mixture was stirred for 48 hours at the same temperature. This reaction mixture was poured into 2 mol/L hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.22 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-53d85600004f4d3f994117258dccbdec
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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