Phenylmethyl 6-chloro-2-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoate → 2-Chloro-6-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoic acid

Participants

Reaction Steps

A solution of 0.6 gram (0.001 mole) of phenylmethyl 6-chloro-2-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoate in 50 mL of ethanol and 15 mL of acetic acid was hydrogenated in the presence of 5% palladium on charcoal using a Parr hydrogenation apparatus. Upon completion of the hydrogenation, the reaction mixture was filtered through diatomaceous earth. The diatomaceous earth filter cake was washed with tetrahydrofuran. The combined filtrate and wash was concentrated under reduced pressure to a residue. The residue was dissolved in 150 mL of methylene chloride and was washed with two 150 mL portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was stirred in 10 mL of diethyl ether containing a few drops of heptane. The resultant solid was collected by filtration and was washed with cold diethyl ether to yield 0.26 gram of 2-chloro-6-(4,6-dimethoxy-1,3,5-triazin-2-yloxy)benzoic acid. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence