Acetic Acid → 2-Hexanone, 4-hydroxy-5-[4-[4-(trifluoromethyl)phenoxy]phenoxy]-

Beteiligte Stoffe

Reaktionsschritte

To a solution of acetone N,N-dimethylhydrazone (0.32 g, 3.23 mmol) in tetrahydrofuran (THF; 5 ml) is added N-butyllithium (0.21 g, 3.23 mmol) at -65°, and the mixture is stirred for 30 minutes. To this is added dropwise 2-[4-(4-trifluoromethylphenoxy)phenoxy]propanal (1.0 g, 3.23 mmol) in 5 ml of THF, keeping the temperature at or below -60°. After 3 hours at -65°, the reaction mixture is allowed to warm to 0°, and is poured onto 20 g ice made slightly acidic with 10% acetic acid. It is extracted into ether, and the organic extract is washed with water and with NaCl and is dried over sodium sulfate. Solvent is removed, and the residue is purified by prep. TLC (silica gel, 20% ethyl acetate/hexane) to give 4-hydroxy-5-[4-(4-trifluoromethylphenoxy)phenoxy]-2-hexanone (C'; Q1 is CH, Y is hydrogen, Z is trifluoromethyl, R 1 is methyl and R2 is methyl). ##STR21##

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