Toluene → HCID 13840075, compound

Participants

Reaction Conditions

Reaction Steps

39.4 g of N-[1-(3,5-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethylidene]-N′-tosylhydrazine (0.084 mol) prepared as in Example 30, 19.9 g of potassium ter-butoxide (0.177 mol) and 3.9 g of Triton X100® are introduced into a three-necked round-bottomed flask comprising 190 ml of toluene. The mixture is brought to reflux for 4 h, cooled to approximately 80° C. and 130 ml of water are introduced. Separation by settling is carried out and the aqueous phase is re-extracted with 90 ml of toluene. The toluene phases are washed with 50 ml of water and concentrated to result in 27.8 g of a brown solid, which is taken up in 30 ml of methanol and maintained for 1 h under agitation. The precipitate is filtered off, washed on the filter with methanol and dried. 16.6 g of (E)-3,5-dimethoxy-3′,4′-methylenedioxy-stilbene is recovered in the form of a brown solid, which exhibits a melting point of 96° C., i.e. a yield of 69% with respect to the starting hydrazone.

Provenance & Evidence