Ethanol → Ethyl 2-chloro-4-hydroxybenzoate

HRID 220818

Reaction equation

HRID 220818 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#N.S(=O)(=O)(O)[OH:12].[CH2:16]([OH:18])[CH3:17]>>[CH2:16]([O:18][C:4](=[O:12])[C:3]1[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:2]=1[Cl:1])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric Acid2×HCID 5927972-Chloro-4-hydroxybenzonitrile

Product 1

HCID 19981058Ethyl 2-chloro-4-hydroxybenzoateYield 38%

Procedure

A solution of 2-chloro-4-hydroxy-benzonitrile (5.0 g, 32.6 mmol) in ethanol (125 ml) was treated with conc. sulphuric acid (25 ml) and the mixture heated at reflux for 3 days. Conc. sulphuric acid (25 ml) was added and the mixture was heated at reflux for another 2 days. The volatiles were removed in vacuo, and the aqueous residue was basified with saturated NaHCO3 and extracted 4 times with diethyl ether. The combined organic extracts were dried and concentrated in vacuo to yield the title compound (2.5 g, 38%).

Workup

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

Sources & evidence

ORD record
ord-05ac95cc2b4844ebac56a4cfd78f468f
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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