Ethanol → Ethyl 4-fluoro-3-hydroxybenzoate

HRID 560315Notes

Reaction equation

HRID 560315 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), sodium bicarbonate (100 g) and ether (300 mL) are added successively, the layers are separated and the aq. 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 aq. 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-a8cb97eff6d94cc7a250d1605961e618
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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