Acetyl chloride → HCID 11140416, compound

HRID 1826079Notes

Reaction equation

HRID 1826079 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:9]([CH:11]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:10]>ClCCl>[C:1]([C:22]1[CH:23]=[C:18]([CH2:17][CH:11]([CH2:9][CH3:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:19]=[CH:20][C:21]=1[O:24][CH3:25])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 11746630HCID 11746630, compound

Product 1

HCID 11140416HCID 11140416, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under stirring and cooling with ice, acetyl chloride (1.00 mL, 14.1 mmol) wad added dropwise to a suspension of aluminum chloride (III) (1.78 g, 13.3 mmol) in dichloromethane (30 mL), and then the mixture was stirred for 30 minutes. Next, a solution of ethyl 2-ethyl-3-(4-methoxyphenyl)propanoate (2.10 g, 8.89 mmol) in dichloromethane (10 mL) was added dropwise. After stirring for 1 hour under cooling with ice, the mixture was allowed to stand overnight at room temperature. The reaction mixture was poured in ice water, the dichloro-methane layer was separated. and the aqueous layer was extracted with dichloromethane. The organic layers were combined and washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=6:1 v/v) to afford 1.21 g (49%) of the title compound as a yellow oily product.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringAfter stirring for 1 hour
  3. temperatureunder cooling with ice
  4. customthe dichloro-methane layer was separated
  5. extractionand the aqueous layer was extracted with dichloromethane
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=6:1 v/v)

Sources & evidence

ORD record
ord-a6a5f078cb89485c9c756c076738a53d
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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