Nitroethane → 2,4-Dihydroxybenzonitrile

HRID 411848

반응식

HRID 411848 반응식
[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]

참가 물질

5

반응물 3

HCID 6587NitroethaneHCID 72132,4-DihydroxybenzaldehydeHCID 517045Sodium Acetate

생성물 1

HCID 30175202,4-Dihydroxybenzonitrile수율 59%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c97384395cba41f795ee1ce6585c05d6
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559315B1

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