Water → 3,3',4,4'-Tetra(hydroxymethyl)-1,1'-biphenyl

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,3′,4,4′-biphenyltetracarboxylic dianhydride (6.0 g, 20.4 mmol, 1.0 molar equivalent) in THF (600 mL) heated to 100° C. is added carefully a solution of LiAlH4 (1M in tetrahydrofuran) (81 mL, 81.6 mmol, 2.0 molar equivalents). The reaction mixture is stirred overnight at 100° C. To this resulting solution cooled at 0° C. is added a 2M sodium hydroxide solution (50 mL) followed by cold water (25 mL) and THF (50 mL). The reaction mixture is then filtered and concentrated under vacuum. The crude product is then washed with THF (20 mL), water (10 mL) and dried over vacuum to give a white powder (3.1 g, 55%). If necessary, the compound can be further purified by recrystallisation in water to give the expected compound as a white powder (3.3 g, 79%). 1H NMR (300.13 MHz, DMSO) δ (ppm) 4.57 (d, J=4.5 Hz, 4H) 4.61 (d, J=4.5 Hz, 4H) 5.09 (t, J=5.2 Hz, 2H) 5.15 (t, J=5.2 Hz, 2H) 7.46 (d, J=8.1 Hz, 2H) 7.52 (dd, J1=8.1, J2=1.8 Hz, 2H) 7.70 (d, J=1.8 Hz, 2H).

Provenance & Evidence