Sulfuric Acid → 2-Pyridinemethanol, 4-ethyl-

HRID 63265

Reaction equation

HRID 63265 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].S(=O)(=O)(O)O.[C:26](=O)(O)[O-:27].[Na+]>CO.O>[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:26][OH:27])[CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 108224-EthylpyridineHCID 62648Ammonium PersulfateHCID 516892Sodium Bicarbonate

Product 1

HCID 123963882-Pyridinemethanol, 4-ethyl-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-ethylpyridine (Commercial, e.g. Sigma-Aldrich) (10.7 g), ammonium peroxydisulfate (45.6 g) and concentrated sulphuric acid (4.5 ml) in methanol (150 ml)/water (70 ml) was refluxed for 24 h. The reaction mixture was slowly added onto aqueous sodium bicarbonate and extracted with chloroform (4×500 ml). This was dried over sodium sulphate, concentrated in vacuo and purified through silica using 0-60% ethyl acetate in hexane to give the title compound, 1.16 g Mass Spec: [MH]+=138.0

Workup

  1. extractionextracted with chloroform (4×500 ml)
  2. dry with materialThis was dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. custompurified through silica using 0-60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a37bdc801ed24874919533c44e84e722
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Linked notes

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