Hydrochloric Acid → 1-(2,6-Dihydroxyphenyl)-propan-1-one

HRID 843121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 843121
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]COC)[C:6]=1[C:15](=[O:18])[CH2:16][CH3:17].Cl>CO.O1CCOCC1.C(OCC)(=O)C>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[C:15](=[O:18])[CH2:16][CH3:17]

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 22614991HCID 22614991, Verbindung

Produkt 1

HCID 116223911-(2,6-Dihydroxyphenyl)-propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 1-(2,6-bis-methoxymethoxy-phenyl)-propan-1-one (770 mg) in methanol (12 ml) and 1,4-dioxane (12 ml) was added 4N-HCl (2 ml) at room temperature, then the mixture was heated to 50° C. and stirred for 2 hours. The mixture was diluted with ethyl acetate and washed with water (20 ml) and brine (20 ml). The separated organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography developed by hexane-ethyl acetate. 1-(2,6-dihydroxyphenyl)-propan-1-one was obtained as a yellow solid (398 mg). EI-MS: m/z 178 (M+); 1H-NMR (CDCl3): δ 1.03-1.08 (2H, m), 1.29-1.35 (2H, m), 2.21-2.31 (1H, m), 6.41 (2H, d, J=8.3 Hz), 7.23 (1H, t, J=8.3 Hz) 9.24 (2H, brs).

Aufarbeitung

  1. washwashed with water (20 ml) and brine (20 ml)
  2. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-55a783d50a1e4261933027fb0022aeda
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376491B1

Notizen zur Reaktion

Wird geladen…