Hydrochloric Acid → HCID 22620557, compound

HRID 840985Notes

Reaction equation

HRID 840985 reaction equation
S(Cl)(Cl)=O.[C:5]1([CH:11]([CH:18]([CH3:20])[CH3:19])[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)(Cl)Cl.ClCCCl>[CH3:19][CH:18]([CH:11]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:15](=[O:17])[CH2:14][CH2:13][CH2:12]1)[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl Chloride2×HCID 6451240Aluminum(III) ChlorideHCID 70170413HCID 70170413, compound

Product 1

HCID 22620557HCID 22620557, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (5.6 ml, 77 mmol) was added to a solution of 5-phenyl-5-(2-propyl)pentanoic acid (8.35 g, 37.9 mmol) in chloroform (50 ml), followed by heating under reflux for 3.5 hours. Then, thionyl chloride (3.0 ml, 41 mmol) was added thereto and the resulting mixture was heated under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in 1,2-dichloroethane (20 ml). The resulting solution was added dropwise to a suspension of aluminum chloride (10.1 g, 75.8 mmol) in 1,2-dichloroethane (100 ml) which had been cooled to 0° C., and the resulting mixture was stirred at 0° C. for 10 minutes. The reaction mixture was poured into a cold 1N hydrochloric acid and extracted twice with ethyl acetate, and the extract solution was washed twice with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/10) to obtain 6.83 g of 9-(2-propyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3.5 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for 1 hour
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. dissolutionthe resulting residue was dissolved in 1,2-dichloroethane (20 ml)
  7. extractionextracted twice with ethyl acetate
  8. washthe extract solution was washed twice with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/10)

Sources & evidence

ORD record
ord-96660b5ed8d54b5d94baea320d95349e
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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