Hydrochloric Acid → 5-Hydroxy-2-hydroxymethylpyridine

HRID 1964790Notes

Reaction equation

HRID 1964790 reaction equation
S([O:11][C:12]1[CH:13]=[N:14][C:15]([CH2:18][O:19]C(=O)C)=[CH:16][CH:17]=1)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+].Cl>O.C(OCC)(=O)C>[OH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[N:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 138159593-Tosyloxy-6-acetoxymethylpyridine

Product 1

HCID 4194905-Hydroxy-2-hydroxymethylpyridineYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-tosyloxy-6-acetoxymethylpyridine (50 g, 0.148 mol) and NaOH (25 g, 0.62 mol) in 150 mL of water was refluxed for 15 h. The reaction mixture was cooled to RT and neutralized with con. HCl. The solvent was evaporated under vacuum affording a solid residue, which was suspended in ethyl acetate (750 mL) and heated to 60° C. for 30 min. with stirring. The suspended material was filtered off and the filtrate was concentrated to give 5-hydroxy-2-hydroxymethylpyridine (15 g, 80%) as a pale yellow solid. It was used in next step without further purification.

Workup

  1. temperaturewas refluxed for 15 h
  2. customThe solvent was evaporated under vacuum
  3. customaffording a solid residue, which
  4. temperatureheated to 60° C. for 30 min.
  5. filtrationThe suspended material was filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-87be0def26a442b9ab28cb4830b24b7d
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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