Pyridine → 4-(2,4,4-trimethylpentan-2-yl)benzoic acid

Participants

Reaction Steps

A mixture of 61.31 grams (0.30 mol) of 4-t-octyltoluene, 161.5 grams of pyridine, and 80.8 grams of 32% KOH was heated on a steam bath. To this mixture was added, in 10 gram portions every 30 minutes, 117.22 grams (0.74 mol) of KMnO4. The reaction mixture was heated overnight and then 10 ml of ethanol was added. After 30 minutes, the mixture was filtered hot and the solid was washed with water. The combined filtrate and washes were heated for another 10 minutes on a steam bath and filtered again with water wash. The yellow filtrate comprised of two layers was acidified with concentrated HCl. On cooling, the upper layer crystallized. This solid was collected, washed with water and dried. The solid was washed with Ligroine (bp=35-60° C.), dissolved in ether, washed with water, dried over MgSO4 and concentrated. The residue was recrystallized from heptanes. Yield was 14.3 grams (20.34%). Melting point=153-155° C. Elemental analysis found C=76.72, H=9.39. This compares to calculated values for C15H22O2 of C=76.88, H=9.46. An NMR spectrum, in CDCl3, was obtained in which agreed with the structure of the expected product.

Provenance & Evidence