p-Toluenesulfonic acid → Octa-1,3,5-triene

Participants

Reaction Conditions

Reaction Steps

A solution of 8.70 g (100 mmol) of morpholine, 0.076 (0.25 mmol) of Pd(acac)2 (acac=acetylacetonate), and 0.35 g (0.875 mmol) of DPPE was admixed with 0.141 g of p-toluenesulfonic acid and 2.4 g of methanol. After forcing in 5.4 g (100 mmol) of butadiene, the mixture was stirred for 17 h at 100° C. under autogenous pressure. There is obtained a yield of 96% at a selectivity of 1 percent by area of octatriene, 3 percent by area of (3,N)-(but-1-enyl)morpholine, 94 percent by area of (1,N)-(but-2-enyl)-morpholine, 1 percent by area of octadienylamine and 1 percent by area of by-products.

Provenance & Evidence