Hydrochloric Acid → 4-Hydroxy-o-toluic acid

HRID 484054

Reaktionsgleichung

Reaktionsgleichung von HRID 484054
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])C)=[C:4]([CH3:11])[CH:3]=1.II.[OH-:14].[Na+].Cl>N1C=CC=CC=1.CCOCC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:14])=[C:4]([CH3:11])[CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 14798Sodium HydroxideHCID 701334-Hydroxy-2-methylacetophenone

Produkt 1

HCID 684754-Hydroxy-o-toluic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4'-Hydroxy-2'-methylacetophenone (15 gm, 0.1 mol) was dissolved in pyridine and iodine (25.4 gm) was added. This mixture was heated to 100° C. for 1 hr and then allowed to stand at room temperature overnight. A thick precipitate was obtained and the mixture was diluted with Et2O before filtering. The solid so obtained was added to 5N NaOH (200 ml) and heated on the steam bath for 1 hr before being cooled and acidified with HCl. This mixture was extracted twice with Et2O and the pooled organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was crystallized from Et2O-hexane to give 9.8 gm of the title compound as a solid.

Aufarbeitung

  1. customA thick precipitate was obtained
  2. filtrationbefore filtering
  3. customThe solid so obtained
  4. temperatureheated on the steam bath for 1 hr
  5. temperaturebefore being cooled
  6. extractionThis mixture was extracted twice with Et2O
  7. washthe pooled organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue was crystallized from Et2O-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0b8061fbc29f44b593d20e2d854fc248
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229381

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