Reaktion #324917

Reaktionsgleichung

4,4-dimethyl-cyclohexanone

4-benzyloxybromobenzene

magnesium

→

1-(4-benzyloxy-phenyl)-4,4-dimethylcyclohexanol

Ausbeute 50.1%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 250 mL round-bottomed flask was placed
2. 2
   TemperaturTo the slurry, cooled in an ice-water bath
3. 3
   workup.STIRRINGThe reaction mixture was stirred for 1 hour at room temperature after which the solvent
4. 4
   Sonstigewas removed under reduced pressure
5. 5
   SonstigeThe residue was partitioned between EtOAc/saturated NH4Cl
6. 6
   ExtraktionThe mixture was extracted twice with EtOAc
7. 7
   Trocknendried (Na2SO4)
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes)

Vorschrift

In a 250 mL round-bottomed flask was placed magnesium turnings (1.85 g, 76.1 mmol), which were stirred under vacuum without solvent overnight. To the turnings was added anhydrous THF (10 mL) and 4-benzyloxybromobenzene (10.0 g, 38.0 mmol) in anhydrous THF (40 ml) over 15 min. After the reaction was complete, the resulting gray slurry was stirred for 2 h at 60° C. To the slurry, cooled in an ice-water bath, was added 4,4-dimethyl-cyclohexanone (3.36 g, 26.6 mmol) in THF (15 mL). The reaction mixture was stirred for 1 hour at room temperature after which the solvent was removed under reduced pressure. The residue was partitioned between EtOAc/saturated NH4Cl. The mixture was extracted twice with EtOAc. The organic phases were combined, dried (Na2SO4) and concentrated. The residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes) to give 4.14 g (50%) of 1-(4-benzyloxy-phenyl)-4,4-dimethylcyclohexanol.

Quelle