Acetyl chloride → HCID 66811127, compound

HRID 1097374Notes

Reaction equation

HRID 1097374 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]1[C:20]2=[C:21]3[C:16](=[CH:17][CH:18]=[CH:19]2)[CH2:15][CH2:14][CH2:13][CH:12]3[CH2:11][CH2:10]1>C(=S)=S>[C:19]1([C:5](=[O:7])[CH3:6])[C:20]2=[C:21]3[CH:12]([CH2:11][CH2:10][CH2:9]2)[CH2:13][CH2:14][CH2:15][C:16]3=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12322894HCID 12322894, compound

Product 1

HCID 66811127HCID 66811127, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

A suspension of aluminum chloride (0.250 g) in carbon disulfide (3 ml) was added with acetyl chloride (0.16 ml). The mixture was stirred at room temperature for 5 minutes, and then slowly added with 2,3,3a,4,5,6-hexahydro-1H-phenalene (0.250 g) dissolved in carbon disulfide (2 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour, and then poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:500) to obtain 1-(5,6,6a,7,8,9-hexahydro-4H-1-phenalenyl)ethanone (0.139 g, yield: 45%) and the title compound (0.135 g, yield: 43%).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:500)

Sources & evidence

ORD record
ord-277a9b9ed37c492ebb55bb69b59ece49
Source dataset
uspto-grants-2012_03
Patent number
US08143260B2

Reaction notes

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