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Hydrochloric Acid → 4-(2-Ethyl-5-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 537680
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 537680
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH3:21])=[C:6]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])[CH:7]=1.N1CCC[C@H]1C(O)=[O:25].[OH-].[Na+].Cl>[Cu]I>[CH2:20]([C:5]1[CH:4]=[CH:3][C:2]([OH:25])=[CH:7][C:6]=1[CH:8]1[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]1=[O:19])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 666785694-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

Produkt 1

HCID 666799374-(2-Ethyl-5-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 4-(5-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (1.0 g, 2.8 mmol), copper(I) iodide (108 mg, 0.57 mmol) and L-proline (33 mg, 0.28 mmol) in an aqueous solution of sodium hydroxide (8.8 ml of a 1N solution) is heated at 200° C. for 2 hours under microwave irradiation. The mixture is cooled to room temperature, poured into 2M aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The solvent is evaporated under reduced pressure and the residue is purified by column chromatography on silica gel to give 4-(2-ethyl-5-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure
  8. customThe solvent is evaporated under reduced pressure
  9. customthe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4d57f5bab26c49e9857a0b54689a0d9e
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08865623B2

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