Reaction #2275702

Reaction equation

4′-chloro-3-methoxy-biphenyl-4-carboxylic acid methyl ester

H2O

LiOH

→

desired product

Yield 91.0%

4′-chloro-3-methoxy-biphenyl-4-carboxylic acid

Yield 91.0%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureThe resulting suspension is heated
2. 2
   Temperatureto reflux for 2 hours
3. 3
   TemperatureThe reaction is cooled
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   Filtrationthe resulting solid is collected by filtration
6. 6
   Washwashed with H2O
7. 7
   Otherdried

Procedure

To a solution of 4′-chloro-3-methoxy-biphenyl-4-carboxylic acid methyl ester, 8, (0.615 g, 2.22 mmol) in THF (20 mL) and H2O (5 mL) at room temperature is added LiOH (0.932 g, 22.2 mmol). The resulting suspension is heated to reflux for 2 hours. The reaction is cooled and concentrated under reduced pressure. The crude product is acidified using conc. HCl and the resulting solid is collected by filtration washed with H2O and dried to afford 0.532 g (91%) of the desired product as a grey solid. 1H NMR (400 MHz, CDCl3) δ ppm 10.69 (1H, br s), 8.26 (1H, d, J=8.1 Hz), 7.53-7.58 (2H, m), 7.44-7.50 (2H, m), 7.33 (1H, dd, J=8.1, 1.6 Hz), 7.20 (1H, d, J=1.3 Hz), 4.17 (3H, s). HPLC-MS: m/z 263 [M+H]+.

Source