Ethanol → Ethyl 4-fluoro-3-hydroxybenzoate

HRID 2064773Notes

Reaction equation

HRID 2064773 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(=O)(=O)(O)O.O.C([O-])(O)=O.[Na+].[CH3:23][CH2:24]O>CCOCC>[CH2:23]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([OH:11])[CH:4]=1)[CH3:24]

Participants

7

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5936354-Fluoro-3-hydroxybenzoic acid

Product 1

HCID 18007712Ethyl 4-fluoro-3-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-fluoro-3-hydroxy-benzoic acid (32.0 mmol) in EtOH (120 mL) is treated with conc. sulfuric acid (25.7 mL) and heated to reflux for 16 h. Water (600 mL), NaHCO3 (100 g) and ether (300 mL) are added successively, the layers are separated and the aqueous layer is extracted twice with ether. The combined organic layers are washed twice with brine, dried over MgSO4 and concentrated in vacuo to give the desired product which is used without further purification. 1H-NMR (DMSO-d6): δ=7.75 (d, J=8.5 Hz, 1H); 7.58-7.63 (m, 1H); 7.12 (t, J=9.3 Hz, 1H); 6.21 (bs, 1H); 4.39 (q, J=7.0 Hz, 2H); 1.40 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. customthe layers are separated
  4. extractionthe aqueous layer is extracted twice with ether
  5. washThe combined organic layers are washed twice with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b7cdb051a3243e0a3a3a81545447479
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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