Methanol → 3-Ethyl-5-fluoro-4-hydroxybenzoic acid methyl ester

HRID 423247Notes

Reaction equation

HRID 423247 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([CH:10]=[CH2:11])[C:7]([OH:12])=[C:6]([F:13])[CH:5]=1.CO>C1COCC1.[C].[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([F:13])[C:7]([OH:12])=[C:8]([CH2:10][CH3:11])[CH:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 586297433-Fluoro-4-hydroxy-5-vinylbenzoic acid methyl ester

Product 1

HCID 586297523-Ethyl-5-fluoro-4-hydroxybenzoic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3-fluoro-4-hydroxy-5-vinylbenzoic acid methyl ester (121 mg) and 10% palladium carbon (20 mg) in THF (1 mL)-methanol (1 mL) was hydrogenated at room temperature over night at medium pressure (3 kgf/cm2). The catalyst was filtered off through a Celite pad, and the filtrate was concentrated to give the title compound (121 mg).

Workup

  1. waitwas hydrogenated at room temperature over night at medium pressure (3 kgf/cm2)
  2. filtrationThe catalyst was filtered off through a Celite pad
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-efdb1a6677f24c2c8660e7c51eaf3ebb
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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