Chloroacetic Acid → 4-Isopropylphenoxyacetic acid

Temperature

40 °C

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.

1. customflask there were placed
2. dissolutionwas dissolved
3. temperatureWithout cooling
4. additionthere were added 60 gms
5. temperaturethe mixture was cooled to room temperature
6. extractionextracted with 2×300 ml
7. customUpon treatment of the ether layer with sodium carbonate solution, the sodium salt of the product precipitated
8. dissolutionThe salt was dissolved in 800 ml
9. customto precipitate product
10. filtrationIt was filtered
11. washwashed with water
12. customdried
13. customto afford 25.6 gms

ORD record

ord-3f08963c3b63468c827afe3c3cddb736

Source dataset

uspto-grants-1982_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04310512