Sodium Hydroxide → (4-(Diphenylamino)phenyl)methanol

Participants

Reaction Steps

To a solution of 2B (3.637 g, 13.3 mmol) in methanol was added dropwise at 0° C. a solution of NaBH4 added to 3.9 g NaOH dissolved in 7.8 mL H2O. The solution was allowed to stir at room temperature overnight. Water was added and the product was extracted with ether (2×) and washed with brine (2×). The combined ether extracts were dried over MgSO4. The solvent was removed and the product was purified using flash chromatography with a hexanes and then ethyl acetate. The ethyl acetate fraction was collected and the solvent removed to reveal 2.667 g (74%) of a honey yellow crystal solid. 1H NMR (CDCl3): δ4.63 (d, 2H), δ6.97–7.06 (m, 6H), δ7.09 (m, 2H), δ7.20–7.28 (m, 6H); m/z 298.1 (M++Na), 276.1 (M++H), 258.1 (M+−H2O).

Provenance & Evidence