Thionyl Chloride → HCID 15324703, 화합물

HRID 861866노트

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HRID 861866 반응식
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:10]([CH2:13][CH2:14][CH2:15][C:16]3=[O:18])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 3041568Benzenebutanoic acid, 4-cyclohexyl-

생성물 1

HCID 15324703HCID 15324703, 화합물수율 100%

시약·촉매·용매 2

HCID 1049Pyridine촉매HCID 1140Toluene용매

실험 절차

To a mixture of 4-(4-cyclohexylphenyl)butyric acid (10.2 g), thionyl chloride (7.4 g) and toluene (50 ml), pyridine (1 drop) was added. After refluxing for 1.5 hours, the solvent was evaporated off under reduced pressure. The residue was dissolved in dichloromethane (20 ml); this solution was added dropwise to a suspension of powdered anhydrous aluminum chloride (8.3 g) in dichloromethane (100 ml) under ice cooling conditions. After stirring at room temperature for 3 hours, the reaction mixture was poured into 1.2N HCl (150 ml), followed by stirring for 30 minutes. The organic layer was collected, while the aqueous layer was extracted with dichloromethane. The extract was combined with the organic layer, succesively washed with water and brine, and dried (MgSO4), after which the solvent was evaporated off. The residual oil was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:10, v/v) to yield 7-cyclohexyl-1-tetralone (9.4 g, 100%) as an oil.

후처리

  1. additionwas added
  2. temperatureAfter refluxing for 1.5 hours
  3. customthe solvent was evaporated off under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  5. additionthis solution was added dropwise to a suspension of powdered anhydrous aluminum chloride (8.3 g) in dichloromethane (100 ml) under ice cooling conditions
  6. additionthe reaction mixture was poured into 1.2N HCl (150 ml)
  7. stirringby stirring for 30 minutes
  8. customThe organic layer was collected, while the aqueous layer
  9. extractionwas extracted with dichloromethane
  10. washsuccesively washed with water and brine
  11. dry with materialdried (MgSO4)
  12. customafter which the solvent was evaporated off
  13. washeluted with ethyl acetate-hexane (1:10

출처 및 근거

ORD 기록
ord-bcb888925d7a44688ee78799509725b8
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716944

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