Reaction #833519

Reaction equation

hexane

nBuLi

THF

2a

4-bromo-1,2-didecyloxybenzene

→

3,3′,4,4′-tetrakisdecyloxybiphenyl

Yield 38.0%

Solvents

water

Conditions

Workup

1. 1
   Otherhad been precooled to −30° C
2. 2
   workup.ADDITIONOnce the addition
3. 3
   Extractionextracted with ether
4. 4
   WashThe ether layer was washed with water
5. 5
   Dryingdried with MgSO4
6. 6
   OtherThe solvent was removed under reduced pressure
7. 7
   OtherThe residue was crystallized from a THF/MeOH mixture at −15° C.

Procedure

A hexane solution of nBuLi (1.57 M, 1.02 mL) was added dropwise to a THF solution (50 mL) of 2a which had been precooled to −30° C. Once the addition was complete the reaction mixture was allowed to warm to room temperature. After stirring for an additional 12 h the reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and dried with MgSO4. The solvent was removed under reduced pressure. The residue was crystallized from a THF/MeOH mixture at −15° C. to give colorless crystals of 3,3′,4,4′-tetrakisdecyloxybiphenyl (3a) in 38% yield (mp 85-86° C.).

Source