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Water → 2-Chloro-1-ethoxy-3-fluoro-4-(4-vinylcyclohexa-1-enyl)benzene

HRID 641106
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HRID 641106 반응식
[Cl:1][C:2]1[C:3]([F:20])=[C:4]([C:11]2(O)[CH2:16][CH2:15][CH:14]([CH:17]=[CH2:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([F:20])=[C:4]([C:11]2[CH2:16][CH2:15][CH:14]([CH:17]=[CH2:18])[CH2:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH3:10]
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참가 물질

5

반응물 3

HCID 962Water2회HCID 6101p-Toluenesulfonic acidHCID 592569731-(3-Chloro-4-ethoxy-2-fluorophenyl)-4-vinylcyclohexanol

생성물 1

HCID 592570462-Chloro-1-ethoxy-3-fluoro-4-(4-vinylcyclohexa-1-enyl)benzene수율 34%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

16.0 g of the compound (24), 0.3 g of p-toluenesulfonic acid and 80 mL of toluene were mixed, and the mixture was refluxed under heating for 1 hour while water distilled out was removed. After cooling the resulting reaction mixture to 25° C., 100 mL of water and 100 mL of toluene were added to and mixed with the reaction mixture. Thereafter, the mixture was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using a mixed solvent of heptane and toluene (heptane/toluene=2/1 by volume) as eluent, and then further purified by recrystallization from ethanol to obtain 5.11 g of 2-chloro-1-ethoxy-3-fluoro-4-(4-vinylcyclohexa-1-enyl)benzene (No. 286) in white color. The yield based on the compound (23) was 45.2%.

후처리

  1. temperaturethe mixture was refluxed
  2. distillationdistilled out
  3. customwas removed
  4. temperatureAfter cooling
  5. customthe resulting reaction mixture to 25° C.
  6. additionmixed with the reaction mixture
  7. customThereafter, the mixture was separated into an organic layer
  8. extractionextraction to the organic layer
  9. washwashed with a 2N sodium hydroxide aqueous solution
  10. dry with materialby drying over anhydrous magnesium sulfate
  11. customThereafter, the solvent was removed by distillation under reduced pressure
  12. customto obtain a residue
  13. customThe resulting residue was purified by silica gel column chromatography
  14. customfurther purified by recrystallization from ethanol

출처 및 근거

ORD 기록
ord-5fe62735c12645b4974f44c14e9f8a43
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07695777B2

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