Sulfuric Acid → 3-Pyridinol, 6-(phenylmethyl)-

HRID 255591Notes

Reaction equation

HRID 255591 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2(O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 20183659HCID 20183659, compound

Product 1

HCID 139788063-Pyridinol, 6-(phenylmethyl)-Yield 45.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-hydroxy-2-[(1-hydroxycyclohexyl)methyl]pyridine (1 g) in acetic acid (15 ml) containing sulfuric acid (5 ml) was heated to reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured on an ice, basified with 10% aqueous sodium hydrogen carbonate, and extracted with ether. The combined ether extracts were washed with aqueous saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The residue was washed with isopropylalcohol to give 2-benzyl-5-hydroxypyridine (409 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. extractionextracted with ether
  4. washThe combined ether extracts were washed with aqueous saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe residue was washed with isopropylalcohol

Sources & evidence

ORD record
ord-f4049c38a2e34371945bf155fbe41750
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

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