Thionyl Chloride → Methyl 2-[3-(phenylchloromethyl)phenyl]propionate

Participants

Reaction Conditions

Reaction Steps

Methyl 2-[3-(phenylhydroximethyl)phenyl]propionate (128 g) was dissolved in 100 mL of dry methylene chloride and the solution was cooled to 0° C. Then 41 mL of thionyl chloride in 50 mL methylene chloride were added along 1 hour, keeping the reaction temperature between 5 and 10° C. After staying for 1 hour at 5° C. and 1 hour at room temperature, solvents were removed and the residue (130.5 g, yellow oil) was vacuum distilled, yielding 103 g (75% yield) of the title compound as a yellow transparent liquid, b.p. 158-163° C./1 tor. In the 200 MHz 1H-NMR apparatus the signal of CH3 -- appears as two doublets of similar intensity, indicating the presence of the two possible diasteromers. By following analogous procedures, compounds IIc of Table 3 were obtained.

Provenance & Evidence