Reaction #833520

Reaction equation

1,4-dimethoxybenzene

Solid 3a

3,3′,4,4′-tetrakisdecyloxybiphenyl

→

4a

Yield 84.0%

1,4-dimethoxy-6,7,10,11-tetrakis(decyloxy)triphenylene

Yield 84.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherThe reaction mixture was quenched with anhydrous MeOH (30 mL)
2. 2
   workup.ADDITIONwas added to the resulting oil
3. 3
   Washwashed with MeOH
4. 4
   OtherThe product was further purified by column chromatography

Procedure

Solid 3a (5.50 g, 7.06 mmol) was added to an ice cold suspension of anhydrous FeCl3 (9.16 g, 56.5 mmol) in dry CH2Cl2 (250 mL). Within 2 min 1,4-dimethoxybenzene (3.90 g, 28.2 mmol) was added to the green reaction mixture. The reaction mixture was allowed to warm slowly to room temperature and then stir for an additional 12 h. The reaction mixture was quenched with anhydrous MeOH (30 mL). The volume of the mixture was reduced to 50 mL under reduced pressure and MeOH (200 mL) was added to the resulting oil. The slightly violet product was called on a frit and washed with MeOH. The product was further purified by column chromatography using a 50% CH2Cl2/50% hexane solvent mixture to afford 4a (RF=0.24) as a colorless solid in 84% yield (mp 69-70° C.).

Source