Potassium Hydroxide → 3-Isopropyl-5-methylphenoxyacetic acid

Participants

Reaction Steps

3-Isopropyl-5-methylphenol (44.0 g, 0.29 mol) and chloroacetic acid sodium salt (35.0 g, 0.3 mol) was dissolved in 180 mL of H2O, and then KOH (86%, 20 g, 0.3 mol) was added slowly. The reaction mixture was refluxed overnight and thereafter concentrated by distillation. After cooling, the mixture was acidified to pH 1, and then extracted with EtOAc. The organic layer was washed H2O, dried over MgSO4, and concentrated. The solid was recrystalized in 5% isopropanol in hexane to give pure 3-isopropyl-5-methylphenoxyacetic acid (38 g, 63%) as white crystals.

Provenance & Evidence