Reaction #2460306

Reaction equation

p-toluenesulfonic acid

biphenyl-4,4′-dicarboxylic acid

n-butanol

toluene

→

dibutyl 4,4′-biphenyldicarboxylate

Solvents

water

dichloromethane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to ambient,
2. 2
   Filtrationfiltered
3. 3
   Washwashed with 10% aqueous NaHCO3
4. 4
   Dryingwith brine, dried (MgSO4)
5. 5
   Concentrationconcentrated
6. 6
   OtherThe crude product was purified by recrystallization from heptane
7. 7
   Otherto obtain 13.4 g (60% of theory) of colorless crystals

Procedure

A mixture of biphenyl-4,4′-dicarboxylic acid (15.2 g, 63 mmol), 100 mL of n-butanol, 200 mL of toluene, and a catalytic amount of p-toluenesulfonic acid was heated at reflux with continuous separation of evolved water (Dean-Stark trap) for 7 d. The reaction mixture was cooled to ambient, diluted with dichloromethane, filtered, washed with 10% aqueous NaHCO3 then with brine, dried (MgSO4), and concentrated. The crude product was purified by recrystallization from heptane to obtain 13.4 g (60% of theory) of colorless crystals. 1H NMR (CDCl3): δ 0.97 (t, 6H), 1.5 (m, 4H), 1.8 (m, 4H), 4.35 (q, 4H), 7.68 (d, 4H), 8.13 (d, 4H).

Source