Benzaldehyde → Hexyl Hexanoate

Participants

Reaction Steps

When a toluene solution of benzyl alcohol and 0.1% complex 2′ was refluxed for 24 hrs in an open system, benzyl benzoate was formed in 70% yield, accompanied by a small amount of benzaldehyde (4%) (Table 24, entry 1). Refluxing 1-hexanol with 0.1% 2 in toluene (115° C.) or neat (157° C.) for 24 hrs resulted in formation of 60-70% of hexyl hexanoate, accompanied by 2.5-10% hexanal (Table 24, entries 2 and 3). Complex 6′ was slightly less catalytically active than 2 (Table 24, entry 7). The PNN complex 4′ exhibited significantly higher catalytic activity than that of the PNP complexes 2′ and 6′; benzyl alcohol, 1-hexanol and 1-butanol were dehydrogenated to the corresponding esters in over 90% yield after heating with 0.1% 4′ in toluene (Table 24, entry 4-6).

Provenance & Evidence