Toluene → 3-(Trifluoromethyl)benzenepropanal

Temperature

-77.5 °C

Methyl 3-[3-(trifluoromethyl)phenyl]propanoate (5 gm) as obtained in example 2 was added to toluene (50 ml) and then cooled to −75 to −80° C. To the solution was added a solution of diisobutylaluminium hydride (4.59 gm) in n-hexane (33 ml) slowly for 1 hour 30 minutes at −75 to −80° C. The reaction mass was maintained for 1 hour at −75 to −80° C. and then added methanol (5 ml) at −75 to −80° C. The temperature of the reaction mass was raised to 0° C. and the reaction mass was poured to the chilled water (150 ml). To the reaction mass was added ethyl acetate (50 ml) and then added sodium sulfate solution (20%, 25 ml). The reaction mass was maintained for 1 hour 30 minutes at room temperature and then filtered through celite bed. The layers were separated and the aqueous layer was extracted with toluene. The combined organic layer was dried over sodium sulfate and the solvent was distilled off under reduced pressure to obtain 4.2 gm of 3-[3-(trifluoromethyl)phenyl]propionaldehyde.

1. temperatureThe reaction mass was maintained for 1 hour at −75 to −80° C.
2. customat −75 to −80° C
3. temperatureThe temperature of the reaction mass was raised to 0° C.
4. temperatureThe reaction mass was maintained for 1 hour 30 minutes at room temperature
5. filtrationfiltered through celite bed
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with toluene
8. dry with materialThe combined organic layer was dried over sodium sulfate
9. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-fa5685e9428f40a6a7f982fca5567540

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921606B2