Ethanol → Ethyl 3-fluoro-4-hydroxybenzoate

HRID 220817

Reaction equation

HRID 220817 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([F:1])[CH:3]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 13745619Ethyl 3-fluoro-4-hydroxybenzoateYield 85%

Procedure

A solution of 3-fluoro-4-hydroxy-benzoic acid (5.16 g, 33.1 mmol) in ethanol (100 ml) was treated with conc. sulphuric acid (5 ml), and the mixture heated at reflux for 4 days. The volatiles were removed in vacuo, and the aqueous residue was basified with saturated NaHCO3 and extracted twice with diethyl ether. The combined organic extracts were dried and concentrated in vacuo to yield the title compound (5.16 g, 85%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 days
  3. customThe volatiles were removed in vacuo
  4. extractionextracted twice with diethyl ether
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c84b9f0d9cf4aa3ae0ff39ecb8f6250
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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