Diethyl Ether → Hydroxy[3-(trifluoromethyl)phenyl]acetic acid

A solution of 3-trifluoromethylbenzaldehyde (69.2 g) in ether (250 ml) was shaken with a solution of sodium metabisulphite (84.5 g) in water (85 ml). The mixture was cooled in the refrigerator overnight, the solid was collected, washed with a little propan-2-ol and dried (120 g). The bisulphite addition complex was suspended in a mixture of water (70 ml) and ether (250 ml) with rapid stirring during the addition of a solution of potassium cyanide (28.5 g) in water (85 ml). The mixture was stirred until all the solid was dissolved and the two layers were clear (ca 2 h). The ethereal layer was separated, evaporated and hydrochloric acid (400 ml) was added. The mixture was stirred on the steam bath for 5 h, cooled. The residue was taken up in the minimum amount of 4N sodium hydroxide solution, washed with ether, acidified with hydrochloric acid and extracted into chloroform. The chloroform extracts were dried and evaporated to an oil (61.8 g) which crystallised on standing.

1. temperatureThe mixture was cooled in the refrigerator overnight
2. customthe solid was collected
3. washwashed with a little propan-2-ol
4. customdried (120 g)
5. additionThe bisulphite addition complex
6. additionwas suspended in a mixture of water (70 ml) and ether (250 ml)
7. stirringThe mixture was stirred until all the solid
8. dissolutionwas dissolved
9. custom(ca 2 h)
10. customThe ethereal layer was separated
11. customevaporated
12. additionhydrochloric acid (400 ml) was added
13. stirringThe mixture was stirred on the steam bath for 5 h
14. temperaturecooled
15. washwashed with ether
16. extractionextracted into chloroform
17. dry with materialThe chloroform extracts were dried
18. customevaporated to an oil (61.8 g) which
19. customcrystallised

ORD record

ord-2017d2fe09cb4f4d9bd43e3804cf4485

Source dataset

uspto-grants-1986_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04588749