Acetyl chloride → 2',5'-Dimethoxyacetophenone

HRID 844425

Reaction equation

HRID 844425 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1>C(Cl)(Cl)(Cl)Cl>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 90161,4-DimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 709912',5'-DimethoxyacetophenoneYield 94.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

19.3 g of AlCl3 are placed in 200 ml of CCl4 at +5° C. under nitrogen and 11.36 g of acetyl chloride are added, followed by portionwise addition of 20 g of 1,4-dimethoxybenzene. After stirring for 3 hours at +5° C., the mixture is poured into dilute ice-cold HCl solution. The organic phase is separated out and dried over MgSO4 and evaporated, and the residue is then chromatographed on silica, eluting with a DCM/heptane mixture (50/50; v/v) to give 24.71 g of the expected product.

Workup

  1. additionthe mixture is poured into dilute ice-cold HCl solution
  2. customThe organic phase is separated out
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customthe residue is then chromatographed on silica
  6. washeluting with a DCM/heptane mixture (50/50; v/v)

Sources & evidence

ORD record
ord-b4824991047d41b385638006a76309f6
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Linked notes

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