3-Fluoro-4-methoxymethoxy-5-vinylbenzoic acid methyl ester → 3-Fluoro-4-hydroxy-5-vinylbenzoic acid methyl ester

HRID 423246Notes

Reaction equation

HRID 423246 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH:10]=[CH2:11])[C:7]([O:12]COC)=[C:6]([F:16])[CH:5]=1>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH:10]=[CH2:11])[C:7]([OH:12])=[C:6]([F:16])[CH:5]=1

Participants

4

Reactant 1

HCID 586297733-Fluoro-4-methoxymethoxy-5-vinylbenzoic acid methyl ester

Product 1

HCID 586297433-Fluoro-4-hydroxy-5-vinylbenzoic acid methyl esterYield 80.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-fluoro-4-methoxymethoxy-5-vinylbenzoic acid methyl ester (185 mg) in THF (2 mL)-3N hydrochloric acid (1 mL) was stirred at 60° C. for 3 hours under heating. The mixture was allowed to stand for cooling down to room temperature, diluted with ethyl acetate, washed successively with water, saturated aqueous sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1, v/v) to give the title compound (121 mg). (In the above, THF is tetrahydrofuran).

Workup

  1. temperatureunder heating
  2. washwashed successively with water, saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-27ad0bce5f344dfa8c0da8c62a23a189
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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