Nitric Acid → 2-Nitro-4-phenylsulfonylphenol

HRID 2224058ノート

反応式

HRID 2224058 の反応式
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[N+:22]([O-])([OH:24])=[O:23]>>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[C:14]([N+:22]([O-:24])=[O:23])[CH:15]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 3438044-(Benzenesulfonyl)phenol

生成物 1

HCID 159333442-Nitro-4-phenylsulfonylphenol収率 112.3%

実験手順

Using the procedure of J. Org. Chem. 59(15) 1994, 4301, 4-benzenesulfonyl-phenol (5.348 g, 22.8 mmol) was added to 3.07 mL of conc. H2SO4 with stirring. Concentrated HNO3 (1.28 g) was added dropwise via addition funnel, and the reaction mixture was stirred under nitrogen for 4 hours. The reaction mixture was then poured over ice, and the resulting suspension was extracted four times with 50 mL of methylene chloride. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to yield an oil which slowly solidified. The solid was washed with 1:1 EtOAc:hexanes to yield 4-benzenesulfonyl-2-nitro-phenol (6.37 g, quantitative) as a crude solid. MS: 235 (M+H)+.

後処理

  1. stirringthe reaction mixture was stirred under nitrogen for 4 hours
  2. additionThe reaction mixture was then poured over ice
  3. extractionthe resulting suspension was extracted four times with 50 mL of methylene chloride
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto yield an oil which
  7. washThe solid was washed with 1:1 EtOAc

出典と根拠

ORDレコード
ord-f272e7771e624153b593827e6d2e537b
出典データセット
uspto-grants-2008_05
特許番号
US07378415B2

反応ノート

読み込み中…