Reaktion #46732

Reaktionsgleichung

2,4-dihydroxy actophenone

1-bromooctane

→

1-(2-Hydroxy-4-octyloxy-phenyl)-ethanone

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONpoured onto H2O (100 mL)
2. 2
   Extraktionthe aqueous phase extracted with diethyl ether (3×)
3. 3
   TrocknenThe combined organic fractions was dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated to dryness
6. 6
   Sonstigepurified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:10)
7. 7
   Sonstigeto yield 4.39 g (66%) as yellow oil

Vorschrift

A slurry of 2,4-dihydroxy actophenone (3.8 g; 25 mmol) and KHCO3 (2.75 g; 27.5 mmol) in DMF (50 mL) was stirred at 50° C. for 1 hour and then added 1-bromooctane (4.75 mL; 27.5 mmol). The reaction mixture was stirred at 50-60° C. for 7 days, poured onto H2O (100 mL) and the aqueous phase extracted with diethyl ether (3×). The combined organic fractions was dried (MgSO4), filtered, evaporated to dryness and purified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:10) to yield 4.39 g (66%) as yellow oil. MS (direct; Cl): 265 (MH+).

Quelle