Sodium Hydroxide → (9-Methyl-9H-carbazol-3-yl)methanol

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Reaction Conditions

Reaction Steps

To a solution of 18.9 g N-methyl-3-formyl carbazole in 400 ml ethanol, a mixture of 2.5 g NaBH4 and 20 ml 0.4N NaOH in water was added dropwise. The mixture was then heated at 60° C. and stirred for one hour. Cooling at room temperature, white crystals were obtained which were filtered, washed with water, dried and recrystallized from a cyclohexane:benzene mixture (1:1), yielding 92% N-methyl-3-hydroxymethyl carbazole with m.p.=96° C. IR: 3346 cm-1 (OH), 710, 729, 747, 770, 804 cm-1 (carbazole) 1H.NMR (CDCl3): 8.13-8.03 ppm (C4, C5, multiplet) 7.43-7.29 ppm (C1, C2, C6, C7, C8, multiplet) 4.84 ppm (CH2 singlet) 3.83 ppm (CH3 singlet) 1.64 ppm (OH, singlet).

Provenance & Evidence