Cumene → HCID 10536243, compound

Participants

Reaction Steps

To a 500 mL round bottom flask was added 100 mL of 1.2 M potassium t-amylate in cyclohexane (0.12 moles) and 41.7 mL of cumene (0.3 moles) under a constant flow of nitrogen gas. Then 10.8 mL of N-methylaniline (0.1 moles) was added to the reaction mixture while the reaction was continuously stirred. n-Butyllithium (46 mL of a 2.2 M solution, 0.1 moles) was added and the resulting amide was left stirring for two days. Cyclohexene oxide (10.1 mL, 0.1 moles) was added. After 24 hours, the reaction was quenched by carefully adding water under the flow of nitrogen. Washing of the product with 100 mL of distilled water yielded two layers of which the organic layer was extracted. Repeated rotovapor distillations removed most of the cumene. Any leftover cumene after rotovapor distillation was removed by vacuum horizontal distillation. This device employs a vacuum (<1 mm Hg) and liquid nitrogen to trap cumene, which distilled at about 85° C., but 16 g of racemic MPAC (0.075 moles, 75% yield) distilled at 120° C. The product, MPAC, was analyzed by NMR spectroscopy and the spectrum confirmed the presence of the compound when it was compared to that of literature (Swamy and Raghavendra, 2002).

Provenance & Evidence