Water → 2-(4-Methoxyphenyl)cyclohexanone

HRID 1794269

반응식

HRID 1794269 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[OH:15])=[CH:5][CH:4]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].O.S(=O)(=O)(O)O>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 25408Sodium DichromateHCID 2542932-(4-Methoxyphenyl)cyclohexan-1-ol

생성물 1

HCID 2542922-(4-Methoxyphenyl)cyclohexanone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

146 g (0.71 mole) of 2-(4-methoxyphenyl)-cyclohexanol from the 1st stage were dissolved in 600 ml of diethyl ether. A solution consisting of 69.9 g (0.23 mole) of sodium dichromate (as dihydrate), 355 ml of water and 53.2 ml of conc. sulfuric acid was added dropwise while stirring vigorously and cooling in an ice bath so that the internal temperature did not exceed 10° C. After completion of the addition the reaction mixture was stirred overnight at room temperature. After separating the phases the aqueous phase was then extracted twice with 200 ml of diethyl ether. The combined organic phases were washed twice with 200 ml of saturated sodium hydrogen carbonate solution and dried over sodium sulfate. After removing the solvent by distillation the remaining oil was distilled and the fraction passing over at 128–134° C./0.05 bar was collected. After crystallisation from n-hexane 130 g of colourless crystals with a melting point of 90° C. were obtained (90% of theory).

후처리

  1. additionwas added dropwise
  2. temperaturecooling in an ice bath so that the internal temperature
  3. customdid not exceed 10° C
  4. additionAfter completion of the addition the reaction mixture
  5. stirringwas stirred overnight at room temperature
  6. customAfter separating the phases the aqueous phase
  7. extractionwas then extracted twice with 200 ml of diethyl ether
  8. washThe combined organic phases were washed twice with 200 ml of saturated sodium hydrogen carbonate solution
  9. dry with materialdried over sodium sulfate
  10. customAfter removing the solvent
  11. distillationby distillation the remaining oil
  12. distillationwas distilled
  13. custompassing over at 128–134° C./0.05 bar
  14. customwas collected
  15. customAfter crystallisation from n-hexane 130 g of colourless crystals with a melting point of 90° C.
  16. customwere obtained (90% of theory)

출처 및 근거

ORD 기록
ord-7768849b17e84d40a39640503902d128
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022739B2

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