Didodecyl 2-(thiophen-3-yl)malonate → Tetradodecyl benzo[1,2-b:4,5-b']dithiophene-4,4,8,8-tetracarboxylate

Participants

Reaction Conditions

Reaction Steps

In a two-necked flask under argon, a solution of Fe(ClO4)3 in methanol (320 mL) was prepared at 0° C. A dispersion of didodecyl 2-(thiophen-3-yl)malonate in methanol (120 mL) was added to the solution. After the resulting solution was stirred at 60° C. for 4 hours under argon, the solvent was evaporated under vacuum at room temperature. After water (100 mL) was added to the residue, the aqueous layer was extracted with CH2Cl2 (100 mL×2) and the organic layer was dried and concentrated. The crude product was purified by flash chromatography (eluent: CH2Cl2:hexane=3:2) to give tetradodecyl benzo[1,2-b:4,5-b′]dithiophene-4,4,8,8-tetracarboxylate (yield: 9.0 g, 50.2%). 1H NMR (CDCl3); 0.9 (12H, t), 1.3 (72H, m), 1.7 (8H, m), 4.2 (8H, t), 7.3 (2H, d), 7.4 (2H, d).

Provenance & Evidence