Hydrochloric Acid → 5-Hydroxy-2-hydroxymethylpyridine

HRID 1964790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1964790
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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 4194905-Hydroxy-2-hydroxymethylpyridineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-87be0def26a442b9ab28cb4830b24b7d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415480B2

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