Hydrochloric Acid → Methyl 4-hydroxy-3-methoxy-5-(trifluoromethyl)benzoate

HRID 423263Notes

Reaction equation

HRID 423263 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7]([O:14]COC)=[C:6]([O:18][CH3:19])[CH:5]=1.Cl>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[C:7]([OH:14])=[C:6]([O:18][CH3:19])[CH:5]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58629771HCID 58629771, compound

Product 1

HCID 29987745Methyl 4-hydroxy-3-methoxy-5-(trifluoromethyl)benzoateYield 48.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methoxy-4-methoxymethoxy-5-trifluoromethylbenzoic acid methyl ester (453 mg) in THF (4 mL) was added 6N-hydrochloric acid (4 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate, washed with water 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=4:1 to 3:1, v/v) to give the title compound (186 mg).

Workup

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

Sources & evidence

ORD record
ord-c0b3135470fa4f37a1d6af6e00152d96
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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