2-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl ester → (E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol

Temperature

0 °C

In 15 ml of toluene were dissolved 3.00 g (12.3 mmol) of ethyl trans-4-(trifluoromethyl)cinnamate, and 16.4 ml (24.6 mmol) of a 1.5 M diisobutyl aluminum hydride-toluene solution were added to the solution with stirring at 0° C. After 20 minutes, ice-water was added to the reaction mixture and the mixture was stirred for 10 minutes, followed by removal of the insolubles by filtration using Celite. The filtrate was extracted with ethyl acetate and, after drying, the solvent was distilled off to obtain a crystalline residue. The residue was recrystallized from a mixed solvent of benzene-hexane to obtain 2.36 g (yield: 96%) of the title compound having a melting point of 53 to 55° C.

1. additionwere added to the solution
2. stirringthe mixture was stirred for 10 minutes
3. customfollowed by removal of the insolubles by filtration
4. extractionThe filtrate was extracted with ethyl acetate
5. customafter drying
6. distillationthe solvent was distilled off
7. customto obtain a crystalline residue
8. customThe residue was recrystallized from a mixed solvent of benzene-hexane

ORD record

ord-d15427de362440939b5b34b50798b4e4

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06300357B1