Acetyl chloride → HCID 66811437, compound

HRID 1097390Notes

Reaction equation

HRID 1097390 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][C:10]12[C:22]3[C:18]([CH2:19][CH2:20][CH2:21]1)=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13][CH2:12][CH2:11]2>C(=S)=S>[CH3:9][C:10]12[C:22]3[C:14](=[CH:15][CH:16]=[C:17]([C:5](=[O:7])[CH3:6])[C:18]=3[CH2:19][CH2:20][CH2:21]1)[CH2:13][CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 58420564HCID 58420564, compound

Product 1

HCID 66811437HCID 66811437, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Conditions

Temperature
-10 °C

Procedure

A suspension of aluminum chloride (1.62 g) in carbon disulfide (25 ml) was added with acetyl chloride (1.00 ml) at −10° C. The mixture was stirred at −10° C. for 20 minutes, and then slowly added with 3a-methyl-2,3,3a,4,5,6-hexahydro-1H-phenalene (1.74 g) dissolved in carbon disulfide (15 ml), and the temperature of the mixture was gradually elevated to room temperature. The reaction mixture was stirred at room temperature for 30 minutes, 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-(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-1-phenalenyl)ethanone (1.63 g, yield: 77%) and the title compound (0.465 g, yield: 22%). The compound was recrystallized from n-hexane to obtain colorless prisms (melting point: 100-101.5° C.).

Workup

  1. customwas gradually elevated to room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:500)

Sources & evidence

ORD record
ord-52b4757b139243f987a0a9a94e0624bb
Source dataset
uspto-grants-2012_03
Patent number
US08143260B2

Reaction notes

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