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

HRID 638522Notes

Reaction equation

HRID 638522 reaction equation
[CH3:1][N:2]1[C:14]2[CH:13]=[CH:12][C:11]([CH:15]=[O:16])=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[BH4-].[Na+].[OH-].[Na+]>C(O)C.O>[CH3:1][N:2]1[C:14]2[CH:13]=[CH:12][C:11]([CH2:15][OH:16])=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 6106669-Methyl-9H-carbazole-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 20252566(9-Methyl-9H-carbazol-3-yl)methanolYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  1. additionwas added dropwise
  2. temperatureCooling at room temperature
  3. customwhite crystals were obtained which
  4. filtrationwere filtered
  5. washwashed with water
  6. customdried
  7. customrecrystallized from a cyclohexane

Sources & evidence

ORD record
ord-7eeafab757d94780bafdd8cfe1a6ee75
Source dataset
uspto-grants-1985_12
Patent number
US04562133

Reaction notes

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