Toluene → Butanal, 4-(acetyloxy)-2-methylene-

Participants

Reaction Conditions

Reaction Steps

A solution of 1,4-diacetoxy-2-butene (0.5 g) and HRh(CO)(PPh3)3-tethered on Zeolite-Y (0.05 g) in toluene (25 ml) was heated in an autoclave at 85° C., under 1200 psig of synthesis gas (50% by volume H2 and 50% by volume CO gas). The reaction was monitored for gas absorption. After the theoretical amount of gas absorption (44 psig) took place and consequently there was no further gas uptake, the reaction was stopped and then the autoclave was cooled to room temperature. The solid catalyst was recovered by decantation of the reaction mixture. The reaction mixture was analyzed by HP 6890 gas chromatograph to give pure 2-Formyl-4-acetoxybutene (99.9% yield and 100% selectivity to 2-Formyl-4-acetoxybutene). Later toluene was removed from the reaction mixture by distillation to get the pure fraction of 2-Formyl-4-acetoxybutene (b.p. 78-79° C./5 mm Hg). The recovered catalyst was recycled five times. It was found that there was no loss in activity upon each recycle. ICP analysis also showed no leaching of the rhodium catalyst.

Provenance & Evidence