Chloroacetic Acid → 4-Isopropylphenoxyacetic acid

Participants

Reaction Conditions

Reaction Steps

Into a 100 ml. flask there were placed 100 gms. sodium hydroxide in 300 ml. water and the mixture was stirred until all of the sodium hydroxide was dissolved. Without cooling, there were added 60 gms. p-isopropylphenol and 95 gms. chloroacetic acid. The mixture was stirred at a temperature between 95 and 105° C. for 1 hour and then cooled to 40° C. The reaction mixture was adjusted to a pH of approximately 2 by addition of 1 molar HCl, the mixture was cooled to room temperature and extracted with 2×300 ml. ether. Upon treatment of the ether layer with sodium carbonate solution, the sodium salt of the product precipitated. The salt was dissolved in 800 ml. water and acidified with hydrochloric acid to precipitate product. It was filtered, washed with water and dried to afford 25.6 gms. product, m.p. 84.5°-87° C.

Provenance & Evidence