Nitric Acid → 2-Nitro-4-phenylsulfonylphenol

HRID 2224058노트

반응식

HRID 2224058 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

HCID 159333442-Nitro-4-phenylsulfonylphenol수율 112.3%

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-f272e7771e624153b593827e6d2e537b
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378415B2

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