Nitroethane → 2,4-Dihydroxybenzonitrile

HRID 491700

反応式

HRID 491700 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])(=O)C.[Na+].[N+:16](CC)([O-])=O>C(O)(=O)C>[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:16]

参加物

5

反応物 3

HCID 6587NitroethaneHCID 72132,4-DihydroxybenzaldehydeHCID 517045Sodium Acetate

生成物 1

HCID 30175202,4-Dihydroxybenzonitrile収率 59%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 2,4-dihydroxybenzaldehyde (5.0 g, 36.2 mmol), sodium acetate (5.94 g, 72.4 mmol), nitroethane (5.44 g, 72.4 mmol) and glacial acetic acid (10 ml) was refluxed for 6 hours. After cooling, the mixture was poured onto ice (100 g) and extracted with ethyl acetate (4×50 ml). The combined organic layers were washed with saturated NaHCO3 until the pH of the aqueous layer remained at 8, dried (Na2SO4) and the solvent removed in vacuo. Flash chromatography (SiO2, cyclohexane:ethyl acetate=1:1) afforded 2,4-dihydroxybenzonitrile (2.87 g, 59%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 6.33 (d, 1H, J=8.6 Hz), 6.43 (s, 1H), 7.37 (d, 1H, J=8.6 Hz), 10.35 (s, 1H), 10.78 (s,1H). IR (KBr) 2200 cm−1.

後処理

  1. temperaturewas refluxed for 6 hours
  2. temperatureAfter cooling
  3. additionthe mixture was poured onto ice (100 g)
  4. extractionextracted with ethyl acetate (4×50 ml)
  5. washThe combined organic layers were washed with saturated NaHCO3 until the pH of the aqueous layer
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-900ffcb4fa794a6a9584cac8438d0e7f
出典データセット
uspto-grants-2009_05
特許番号
US07531563B2

関連ノート

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