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

HRID 2259604Notes

Reaction equation

HRID 2259604 reaction equation
[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

Participants

3

Reactant 1

HCID 113215684-(3-chlorophenyl)butanoic Acid

Product 1

HCID 122911496-Chloro-1-tetraloneYield 54.9%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 35.72 g 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 h. 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 h, 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.

Workup

  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 h
  10. additionthe reaction was 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

Sources & evidence

ORD record
ord-85084cccb6ab41d2a283a19e005767c8
Source dataset
uspto-grants-1995_12
Patent number
US05474998

Reaction notes

Loading…