Hydrochloric Acid → 1-(3-(Trifluoromethylthio)phenyl)propan-2-one

13.2 g. (50 mmols) of 1-(3'-trifluoromethylthiophenyl)-2-nitro-propene, 19.6 g. (0.35 g. atom) of iron powder and 0.25 g. of ferric chloride are introduced into a 250 ml. three-necked flask equipped with a mechanical stirrer, a condenser and a dropping funnel, and this mixture is heated on an oil bath at 80°-90°C. 13.5 ml. of concentrated hydrochloric acid are added dropwise, via the dropping funnel, with stirring, over the course of 7 hours, while the temperature is kept at 90°C. The reaction mixture is allowed to cool and rendered alkaline with sodium hydroxide solution. The ketone is then steam distilled. The distillate is extracted twice in succession with 100 ml. of diethyl ether each time. The two ether extracts are combined, dried over sodium sulphate and filtered. The solvent is evaporated from the filtrate in vacuo on a water bath, and the residue is rectified. 7.1 g. (60.5% yield) of 1-(3'-trifluoromethylthiophenyl)-2-propanone are thus obtained as a colourless oil, b.p. 138°-146°C./25-30 mm. Hg., nD23 ° = 1.489.

1. customthree-necked flask equipped with a mechanical stirrer, a condenser and a dropping funnel
2. temperaturethis mixture is heated on an oil bath at 80°-90°C
3. customis kept at 90°C
4. temperatureto cool
5. distillationsteam distilled
6. extractionThe distillate is extracted twice in succession with 100 ml
7. dry with materialdried over sodium sulphate
8. filtrationfiltered
9. customThe solvent is evaporated from the filtrate in vacuo on a water bath

ORD record

ord-6c62b65a98934f668de8197d2e9dc4a6

Source dataset

uspto-grants-1976_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03965190