Reaction #65018

Reaction equation

ethylmagnesium bromide

2-chloro-1-phenyl-1,2,3,4-tetrahydronaphth-1-ol

→

title compound

Yield 187.8%

2-phenyl-1,2,3,4-tetrahydronaphthalen-1-one

Yield 187.8%

Solvents

benzene

Conditions

Workup

1. 1
   Temperatureheat
2. 2
   Temperatureto reflux for 5 hours
3. 3
   TemperatureCool the mixture to room temperature
4. 4
   Otherquench with saturated NH4Cl (aqueous)
5. 5
   ExtractionExtract with ether
6. 6
   Washwash with water and brine
7. 7
   Dryingdry over Na2SO4
8. 8
   Concentrationconcentrate

Procedure

Step C Add ethylmagnesium bromide (1.76 mL, 5.27 mmol, M in) dropwise to a 0° C. solution of 2-chloro-1-phenyl-1,2,3,4-tetrahydronaphth-1-ol (1.36 g, 5.27 mmol) in dry benzene (20 mL). Stir the solution at 0° C. for 30 min and heat to reflux for 5 hours. Cool the mixture to room temperature and quench with saturated NH4Cl (aqueous). Extract with ether, combine the ethereal extracts, wash with water and brine, dry over Na2SO4 and concentrate to provide 1.1 g (94%) of the title compound.

Source