Water → 4-(6-Hydroxyhexyloxy)biphenyl-4'-carboxylic acid

Participants

Reaction Steps

To a solution of 8 (13.0 g, 4.4 mmol) in ethylene glycol (370 ml) was added KOH (37.07 g, 66.06 mmol). After refluxing for 2 h, the reaction mixture was poured into 1.6 L water for acidification to a pH less than 4. The precipitate from acidification was boiled in methanol to remove water and ethylene glycol. The solid residue collected by filtration was further purified by boiling in methylene chloride. The solid product was further washed with hot methylene chloride to yield 9 (12.94 g, 93.4%). 1H NMR spectral data (400 MHz, DMSO-d6): δ 1.30-1.50 (m, 6H, —CH2—), 1.74 (m, 2H, —CH2—), δ 3.40 (t, 2H, —CH2OAr), δ 4.01 (t, 2H, HOCH2—), δ 7.05 (d, 2H, aromatic rings), δ 7.67 (d, 2 H, aromatic rings), δ 7.74 (d, 2H, aromatic rings), δ 7.98 (d, 2H, aromatic rings).

Provenance & Evidence