4-(3-chlorophenyl)butanoic Acid → 6-Chloro-1-tetralone

HRID 1087803

반응식

HRID 1087803 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][CH:7]=1>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2

참가 물질

3

반응물 1

HCID 113215684-(3-chlorophenyl)butanoic Acid

생성물 1

HCID 122911496-Chloro-1-tetralone

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

A mixture of 35.72 of the product from Step B and 50 ml of thionyl chloride was heated at reflux for 2 hours and then stirred at room temperature for 18 hrs. After this time thionyl chloride was removed at reduced pressure and the product was dissolved in carbon tetrachloride and concentrated at reduced pressure. The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. and 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions. After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl and extracted three times with methylene chloride. The organic extracts were dried over magnesium sulfate and concentrated to approximately 30 g of a brown oil. Chromatography on silica gel with 10% ethyl acetate/hexane afforded 17.83 g of 6-chloro-3,4-dihydro-1(2H)-naphthalenone as a brown oil. 1H NMR was consistent with the structure.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customAfter this time thionyl chloride was removed at reduced pressure
  4. dissolutionthe product was dissolved in carbon tetrachloride
  5. concentrationconcentrated at reduced pressure
  6. dissolutionThe residue was dissolved in 150 ml of dichloroethane
  7. temperaturecooled to 0° C.
  8. addition28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions
  9. stirringAfter stirring for 3 hrs the reaction
  10. additionwas poured over a mixture of ice/1N HCl
  11. extractionextracted three times with methylene chloride
  12. dry with materialThe organic extracts were dried over magnesium sulfate
  13. concentrationconcentrated to approximately 30 g of a brown oil

출처 및 근거

ORD 기록
ord-6bbf4c448ae94b2893d709237b90e89b
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04960784

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