Sulfuric Acid → 1-(2,4-Dichlorophenyl)prop-2-en-1-one

HRID 561510노트

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HRID 561510 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:12])[CH:10]=[CH2:11].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].S(=O)(=O)(O)O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:12])[CH:10]=[CH2:11]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 24502Potassium DichromateHCID 202826161-(2,4-Dichlorophenyl)prop-2-en-1-ol

생성물 1

HCID 202826771-(2,4-Dichlorophenyl)prop-2-en-1-one수율 55%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
17.5 °C

실험 절차

73.5 g (362 mmol) of the compound from Example 185A in 2.21 of dichloromethane were mixed with 105 g (1.21 mol) of activated manganese dioxide and heated under reflux for 20 h. A further 105 g (1.21 mol) of activated manganese dioxide was added in each case after 2 and 4 h. Filtration with suction through kieselguhr, washing with dichloromethane and concentration resulted in 57.0 g of a mixture of the title compound and the compound from Example 185A. 47.7 g (162 mmol) of potassium dichromate were added to 47.0 g of this mixture in 329 ml of 10% strength sulfuric acid, occasionally cooling at 15-20° C., and the mixture was stirred for 1.5 h. This was followed by addition of 400 ml of ethyl acetate, neutralization by adding sodium bicarbonate, filtration through kieselguhr, washing with ethyl acetate, separation of the phases, drying of the organic phase and concentration. The crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 6/1) to result in 17.8 g (55%) of the title compound.

후처리

  1. additionby adding
  2. filtrationsodium bicarbonate, filtration through kieselguhr
  3. washwashing with ethyl acetate, separation of the phases
  4. customdrying of the organic phase and concentration
  5. customThe crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 6/1)

출처 및 근거

ORD 기록
ord-a2d7eb8188494407a3d99a93d3182786
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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