Reaction #833521

Reaction equation

THF

4a

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

→

5a

Yield 80.0%

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

Yield 80.0%

Solvents

ether

Conditions

Workup

1. 1
   Washwashed with a saturated solution of NaHCO3 and water
2. 2
   DryingThe organic layer was dried with MgSO4
3. 3
   Otherthe solvent removed under reduced pressure
4. 4
   OtherThe crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane)

Procedure

An aqueous solution (1 mL) of (NH4)2Ce(NO3)6 (0.035 g, 0.064 mmol) was added dropwise to a THF solution (5 mL) of 4a (0.029 g, 0.032 mmol). The reaction mixture immediately turned deep red. After 6 h the reaction mixture was poured into ether and washed with a saturated solution of NaHCO3 and water. The organic layer was dried with MgSO4 and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane) to afford 5a as a deep red solid in 80% yield (mp 86-87° C.).

Source