Lithium Hydroxide → 3,5-Didecanyldithieno[3,2-b:2',3'-d]thiophene-2,6-dicarboxylic acid

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Reaction Steps

Compound 67 (10.2 g, 0.017 mol) is mixed with LiOH (1.0 g in 10 mL water), THF (100 mL), MeOH (20 mL) and a catalytic amount (−35 mg) of tetrabutylammonium iodide. This mixture is heated at reflux overnight, then most of the solvent is evaporated. The residue is acidified with concentrated HCl (30 mL), forming a solid which is collected by filtration, washed thoroughly with water, and vacuum dried to yield compound 68 (8.6 g, 98% yield). M.P.: 280.1° C. 1H NMR (CD2Cl2): δ 3.24 (t, 4H), 1.72 (m, 2H), 1.29 (m, 30H), 0.88 (t, 6H). 13C NMR: 168.46, 148.24, 146.58, 136.32, 35.91, 33.64, 28.91 (m, overlap), 26.60, 17.49.

Provenance & Evidence