Hydrochloric Acid → 2,6-Di-t-butyl-4-(3'-cyano-4'-nitrophenyl)phenol

HRID 1719661ノート

反応式

HRID 1719661 の反応式
[OH-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])#[N:4].[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]=1[OH:28])([CH3:17])([CH3:16])[CH3:15].Cl>CS(C)=O>[C:24]([C:20]1[CH:21]=[C:22]([C:9]2[CH:8]=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[C:5]([C:3]#[N:4])[CH:10]=2)[CH:23]=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:19]=1[OH:28])([CH3:27])([CH3:26])[CH3:25]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11922o-NitrobenzonitrileHCID 14798Sodium HydroxideHCID 314052,6-Di-tert-butylphenol

生成物 1

HCID 134667172,6-Di-t-butyl-4-(3'-cyano-4'-nitrophenyl)phenol収率 24.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 30 mg (0.75 mmol) of powdered sodium hydroxide, 87 mg (0.59 mmol) of 2-cyano-1-nitrobenzene, 155 mg (0.75 mmol) of 2,6-di-t-butylphenol, and 1.0 mL of dimethylsulfoxide was heated at 80° C. for two hours and poured into 10 mL of 1N HCl, and the resulting aqueous mixture was extracted with three 10 mL portions of diethyl ether. The ether layers were combined, dried over magnesium sulfate, and concentrated. Purification of the residue by preparative thin layer chromatography and crystallization afforded 51 mg (24% yield) of 2,6-di-t-butyl-4-(3'-cyano-4'-nitrophenyl)phenol.

後処理

  1. extractionthe resulting aqueous mixture was extracted with three 10 mL portions of diethyl ether
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customPurification of the residue
  5. customby preparative thin layer chromatography and crystallization

出典と根拠

ORDレコード
ord-588db222e8484d6c85faa94fdc906d26
出典データセット
uspto-grants-1985_09
特許番号
US04541962

反応ノート

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