2-butoxy-5-chlorobenzoic acid synthesis

Yield:27830-13-3 79%

Reaction Conditions:

Stage #1: C₁₂H₁₅ClO₃with methanol;sodium hydroxide;water at 20; for 4 h;
Stage #2: with hydrogenchloride in water; pH=2;

Steps:

16

A solution of NaOH (8.3 g, 0.21 mol) in water (100 mL) is added to a solution of methyl 2- butoxy-5-chlorobenzoate 16.64 (23.5 g, 0.10 mol) in MeOH (70 mL) and the resulting mixture is stirred at room temperature for 4 h. After evaporation of most of the solvent, the resulting suspension is diluted with water (150 mL), acidified to pH 2 with cone. HCl and extracted with EtOAc. The organic layer is separated, dried over Na₂SO₄, filtered and evaporated to dryness to give 16.65 (18.2 g, 79%) as an off-white solid.

References:

WO2009/52078,2009,A1 Location in patent:Page/Page column 94