Sodium Hydroxide → HCID 22114962, compound

Participants

Reaction Steps

2.06 g (51.5 mmol) of sodium hydroxide in 150 ml of methanol were added dropwise to 13.50 g (42.9 mmol) of methyl 2,4-dichloro-3-(3-i-propyl-1,2,4-oxadiazol-5-yl)benzoate in 330 ml of methanol. The mixture was stirred at room temperature for 12 hours and a further 0.52 g (12.9 mmol) of sodium hydroxide were added. The mixture was subsequently stirred at room temperature for a further 48 hours and the solvent was then removed. The residue was taken up in 200 ml of 5% strength potassium carbonate solution and washed once with ethyl acetate and twice with methylene chloride. The aqueous phase that remained was then acidified (pH=2) using hydrochloric acid and extracted repeatedly with methylene chloride. The combined organic phases were dried and concentrated. 7.20 g (56% of theory) of 2,4-dichloro-3-(3-i-propyl-1,2,4-oxadiazol-5-yl)benzoic acid were obtained.

Provenance & Evidence