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

HRID 638522ノート

反応式

HRID 638522 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7eeafab757d94780bafdd8cfe1a6ee75
出典データセット
uspto-grants-1985_12
特許番号
US04562133

反応ノート

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