Sulfuric Acid → 4-Hydroxy-2'-nitrobutyrophenone

HRID 342189노트

반응식

HRID 342189 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][CH2:12][CH2:13][OH:14])([O-:3])=[O:2].[OH:15]S(O)(=O)=O>O1CCCC1.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:15])[CH2:11][CH2:12][CH2:13][OH:14])([O-:3])=[O:2]

참가 물질

5

반응물 2

HCID 1118Sulfuric Acid2회HCID 117454514-(2-Nitrophenyl)but-3-yn-1-ol

생성물 1

HCID 109767084-Hydroxy-2'-nitrobutyrophenone수율 37%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

A mixture of HgO (0.21 g, 1.0 mmol) in 50 ml of 0.12N H2SO4 is heated to 60° C., treated dropwise with a solution of 4-(o-nitrophenyl)-3-butyne-1-ol (3.70 g, 19.4 mmol) in 25 ml of tetrahydrofuran over a 10 minute period, held at 60° C. for 3 hours, treated with additional HgO (0.84 g, 3.9 mmol) suspended in 25 ml of 0.12N H2SO4, held at 60° C. for 4 hours, cooled to room temperature and diluted with water. The resultant aqueous mixture is extracted with ether. The extracts are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to give a residue. The residue is purified by flash column chromatography (silica gel; gradient 1:1→2:1 ethyl acetate: hexanes as eluent) to give the title product as a brown oil, 1.48 g, 37% yield, identified by NMR and mass spectral analyses.

후처리

  1. additiontreated with additional HgO (0.84 g, 3.9 mmol)
  2. waitheld at 60° C. for 4 hours
  3. temperaturecooled to room temperature
  4. extractionThe resultant aqueous mixture is extracted with ether
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give a residue
  9. customThe residue is purified by flash column chromatography (silica gel; gradient 1:1→2:1 ethyl acetate: hexanes as eluent)

출처 및 근거

ORD 기록
ord-00c644a877304e7c9b86507b26f1e67f
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856576

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