Sodium Hydroxide → HCID 67768016, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of NaOH (2.73 g, 68.25 mmol) in 80 ml of water and 40 ml of methanol was added in one portion 8 g (22.56 mmol) of 2,6-dichloro-3-(2-pyrrolidinoethoxy)benzoic acid methyl ester hydrochloride and the mixture was heated at 90° C. for 15 hours. The mixture was concentrated in vacuo to remove methanol, the aqueous layer was acidified with 20 ml of conc. HCl solution, and the white solid was filtered. The white solid was dissolved in hot water, filtered, and the filtrate was treated with 15 ml of conc. HCl solution. The solid product was recrystallized from methanol/ether to afford 6.53 g (85%) of 2,6-dichloro-3-(2-pyrrolidinoethoxy)benzoic acid hydrochloride (Formula III: Ar=2,6-Cl2 -3- (OCH2CH2 -1-pyrrolidinyl)phenyl) as a white crystalline solid, m.p. 257°-259° C.

Provenance & Evidence