Einecs 211-027-4 → HCID 223474, compound

Participants

Reaction Conditions

Reaction Steps

An excess of triethyl phosphite was added to 3-chlorobenzyl chloride (a), and the mixture was heated with stirring at 130° C. until the generation of ethyl bromide stopped. Diethylchlorobenzyl phosphonate (b) was obtained by the removal of excess triethyl phosphite. Dried dimethylformamide and an excess of sodium methylate were added thereto as a solvent and as a base, respectively, followed by cooling at 0° C. on an ice bath. An equivalent of m-anisaldehyde (c) was added thereto, and the mixture was stirred at room temperature for 1 hour. Then, after stirring at 90° C. for 1 hour, the temperature was lowered to room temperature and stirring was continued overnight. The reaction solution was extracted with ethyl acetate to obtain an ethyl acetate extract. This extract was purified by silica gel chromatography (solvent: hexane/ethyl acetate=9.5/0.5 (V/V)) to obtain 3'-chloro-3-methoxystilbene (d). Subsequently, an excess of pyridinium chloride was added to 3'-chloro-3-methoxystilbene (d), and heated with stirring at 180° C. for 3 hours. The reaction solution was extracted with ethyl acetate, and the resulting ethyl acetate extract was purified by silica gel chromatography (solvent: hexane/ethyl acetate=8.5/1.5 (V/V)) to obtain 3'-chloro-3-hydroxystilbene (compound 4).

Provenance & Evidence