Toluene → HCID 66674281, compound

Participants

Reaction Conditions

Reaction Steps

19 g of N-[1-(3,5-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethylidene]-N′-tosylhydrazine (0.39 mol) prepared as in Example 29. 9.3 g of potassium ter-butoxide (0.83 mol) and 1.9 g of Triton X100® are introduced into a three-necked round-bottomed flask comprising 100 ml of toluene. The mixture is brought to reflux for 3 h, cooled to approximately 90° C. and 70 ml of water are introduced. Separation by settling is carried out and the aqueous phase is re-extracted with 50 ml of toluene. The toluene phases are washed with 50 ml of water and concentrated to result in 12.3 g of a viscous product with a yellow color, which is taken up in 10 ml of methanol and maintained for 3 h under agitation. The precipitate is filtered off, washed on the filter with methanol and dried. 6.5 g of (E)-3,5-dimethoxy-4′-isopropyloxy-stilbene is recovered in the form of a white solid, which exhibits a melting point of 61° C., i.e. a yield of 55.6% with respect to the starting hydrazone.

Provenance & Evidence