3',5'-Dihydroxyacetophenone → 5-Ethylbenzene-1,3-diol

HRID 1798025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798025
[OH:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH3:10])[CH:5]=[C:6]([OH:8])[CH:7]=1>Cl.O.[Pd]>[CH2:9]([C:4]1[CH:5]=[C:6]([OH:8])[CH:7]=[C:2]([OH:1])[CH:3]=1)[CH3:10]

Komponenten

4

Edukt 1

HCID 1039933',5'-Dihydroxyacetophenone

Produkt 1

HCID 127958985-Ethylbenzene-1,3-diolAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21885828Hydrate;hydrochlorideLösungsmittel

Versuchsvorschrift

A mixture of 1-(3,5-dihydroxy-phenyl)-ethanone (5 g, 32.89 mmol), 10% Pd—C (1 g) in 4% HCl—H2O (100 mL) was hydrogenated at 1 atmosphere for 16 hours. The mixture was extracted with EtOAc and the organic extracts was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 5-ethyl-benzene-1,3-diol (2.37 g, 52%). 1H NMR (400 MHz, CDCl3δ 6.26 (s, 2H), 6.20 (s, 1H), 4.78 (s, 2H), 2.55 (m, 2H), 1.20 (m, 3H).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe organic extracts was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6f502665671c4d1a93e86c2c7d3b4f6d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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