Sulfuric Acid → 2-Hydroxy-3-nitrobenzonitrile

HRID 650096

反応式

HRID 650096 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].[N+:10]([O-])([O-:12])=[O:11].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[C:4]=1[OH:9])([O-:12])=[O:11]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 119072-HydroxybenzonitrileHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

生成物 1

HCID 124686862-Hydroxy-3-nitrobenzonitrile収率 42.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-Cyanophenol (4.72 g, 40 mmol) was dissolved in methylene chloride(80 ml) followed by the addition of sodium nitrate (3.76 g, 44 mmol). The addition of sulfuric acid (40 ml/ 3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hrs, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2Cl2) gave the desired product(2.8 g, 42%). 1H NMR (CD3COCD3): δ8.47 (d, 1H), 8.15 (d, 1H), 7.30 (t, 1H).

後処理

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-7e87f2c0504243fd877d10236d70fbd8
出典データセット
uspto-grants-2001_08
特許番号
US06271261B1

関連ノート

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