Adipic Acid → 1-Decene

Participants

Reaction Steps

The results of the oxidation of the simple alkyl aromatic olefins to carboxylic acids using the process of the present invention are shown in Table 1 and FIGS. 7a and 7b. The process of the present invention oxidized both cis- and trans-stilbene (1 and 2) to two equivalents of benzoic acid (1a) in 95% yield. Trans-cinnamic acid (3), styrene (4), and methyl cinnamate (5) were also easily oxidized by the process of the present invention to 1a in 97%, 94% and 96% yields, respectively. Cyclohexene (6) was oxidized by the process of the present invention to the desired adipic acid (6a) but in a reduced yield, 50%, presumably due to its water solubility. However, cyclooctene (7) was easily oxidized by the process of the present invention to suberic acid (7a) with a yield of 82%. Additionally, simple alkyl olefins such as 1-decene (8), 1-nonene (9), and trans-2-nonene (10), all provided the appropriate alkyl carboxylic acids 8a, 9a, and 10a, respectively, in 93%, 90%, and 93% yields, respectively. Similarly, methyl oleate (11) provided a clean conversion to nonanoic acid (8a) and nonanedoic acid monomethyl ester (11a).

Provenance & Evidence