Acetyl chloride → HCID 54041171, compound

HRID 1756764Notes

Reaction equation

HRID 1756764 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]([O:11][C:12](=[O:30])[CH2:13][CH:14]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:21]=1[O:28][CH3:29])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:10]>C(Cl)Cl>[CH2:9]([O:11][C:12](=[O:30])[CH2:13][CH:14]([C:20]1[CH:25]=[C:24]([C:5](=[O:7])[CH3:6])[CH:23]=[C:22]([O:26][CH3:27])[C:21]=1[O:28][CH3:29])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:10]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 54099120HCID 54099120, compound

Product 1

HCID 54041171HCID 54041171, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 800 mg (6.00 mmol) of anhydrous aluminum chloride in 5 ml of methylene chloride were added 0.43 g (6.05 mmol) of acetyl chloride with stirring and ice cooling and then dropwise a solution of 925 mg (3.00 mmol) of 3-(2, 3-dimethoxyphenyl)octanoic acid ethyl ester in 3 ml of methylene chloride. The resultant mixture was allowed to react under ice cooling for 20 minutes and added portionwise into ice water. The organic layer was separated, and the aqueous layer was extracted with methylene chloride. The organic layers were combined, washed with water and aqueous saturated sodium hydrogencarbonate, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane (1/5) to give 900 mg of 3-(5-acetyl-2, 3-dimethoxyphenyl)octanoic acid ethyl ester as a colorless oil. Yield, 86%.

Workup

  1. customto react under ice cooling for 20 minutes
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. washwashed with water and aqueous saturated sodium hydrogencarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with ethyl acetate/hexane (1/5)

Sources & evidence

ORD record
ord-a36364ce05904b829eee8f3458d83cf1
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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