Nitroethane → 2,4-Dihydroxybenzonitrile

HRID 411848

反応式

HRID 411848 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 pK 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) δ6.33 (d, 1 H, J=8.6 Hz), 6.43 (s, 1 H), 7.37 (d, 1 H, J=8.6 Hz), 10.35 (s, 1 H), 10.78 (s, 1 H). 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 pK 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-c97384395cba41f795ee1ce6585c05d6
出典データセット
uspto-grants-2003_05
特許番号
US06559315B1

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