Ethanol → HCID 11977441, compound

Participants

Reaction Steps

To a clean, dry 500 mL round bottom flask equipped with a stir bar, Dean-Starke adapter, condenser, drying tube, and nitrogen inlet, was added 10.0 mL (0.015411 mol) of a 40 wt % aqueous solution of tetrabutylammonium hydroxide, 1.2801 (0.007705 mol) terephthalic acid, 100 mL ethanol, and 150 mL benzene. Lowered apparatus into an oil bath and heated to reflux for 6 hours. The azeotrope distilled at 64.9° C. and the reaction was allowed to remove water overnight. The reaction was cooled to room temperature, and the solvent was removed via rotary evaporation. A sample of the crude product was shown to be very soluble in water, and an NMR was taken which showed the absence of terephthalic acid. The wax-like solid was recrystallized from ethanol/ether to give white crystals, 3.9104 g (78%). Calculated for C40H76N2O4: C, 740219%; H, 11.8019%; N, 4.3161%. Found: C, 69.16; H, 11.74%; N, 4.02%. 1H NMR (CDCl3 300 MHZ): δ 0.92(t 24H), δ 1.30-1.50 (mm 32H), δ 3.10 (t 16H), 6 8.00 (m 4H). Melting point 135-137° C.

Provenance & Evidence