Water → 4,4'-Oxybis(benzene-1,2-dimethanol)

Participants

Reaction Steps

To a solution of LiAlH4 (1M in THF) (64 mL, 64.0 mmol, 4.0 molar equivalents) in THF (50 mL) cooled to −78° C. is added dropwise a solution of 4,4′-oxydiphthalic anhydride (5.0 g, 9.6 mmol, 1 molar equivalent) in THF (20 ml). The reaction mixture is allowed to warm up to room temperature and then stirred at 70° C. for 2 hrs. To this resulting solution cooled at 0° C. is added a 2M sodium hydroxide solution (40 mL) followed by cold water (25 mL) and THF (50 mL). The reaction mixture is then further extracted with THF (3×50 mL). The organic fractions are combined, washed with brine, dried as added over magnesium sulfate, filtered and concentrated in vacuum to give a light brown oil. The crude oil is dissolved in acetone and Et2O is added until an off-white precipitate started to form. After filtration, the organic layer is concentrated in vacuum to give a light brown oil which crystallises spontaneously. Purification by DCM washes gave the title compound as a light yellow powder (2.75 g, 59%). 1H NMR (300.13 MHz, DMSO-d6) (ppm) 4.47 (d, J=5.40 Hz, 4H) 4.53 (d, J=5.40 Hz, 4H) 5.03 (t, J=5.40 Hz, 2H) 5.12 (t, J=5.40 Hz, 2H) 6.84 (dd, J1=2.70 Hz, J2=8.40 Hz, 2H) 7.04 (d, J=2.70 Hz, 2H) 7.34 (d, J=8.40 Hz, 2H).

Provenance & Evidence