Hydrochloric Acid → 2,4,5-Trimethoxyacetophenone

HRID 1957489Notes

Reaction equation

HRID 1957489 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][CH:8]=1.[C:17](Cl)(=[O:19])[CH3:18].Cl>C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:8]=1[C:17](=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 672841,2,4-TrimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 745602,4,5-TrimethoxyacetophenoneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methylene chloride, 47.5 g of aluminum chloride were added, followed by the addition of 30 g of 2,4,5-trimethoxybenzene and then 13 ml of acetyl chloride under ice cooling. The resulting mixture was stirred at room temperature for 6 hours. After the completion of the reaction, 1N hydrochloric acid was added to the reaction mixture under ice cooling. The resulting mixture was then extracted with methylene chloride. The extract so obtained was washed successively with 1N hydrochloric acid, a 1N aqueous solution of sodium hydrochloride and saturated saline and then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The crude product so obtained was washed with ethanol, whereby 18.6 g of 2',4',5'-trimethoxyacetophenone were obtained (yield: 50%).

Workup

  1. additionwas added to the reaction mixture under ice cooling
  2. extractionThe resulting mixture was then extracted with methylene chloride
  3. extractionThe extract so
  4. customobtained
  5. washwas washed successively with 1N hydrochloric acid
  6. dry with materiala 1N aqueous solution of sodium hydrochloride and saturated saline and then dried over anhydrous magnesium sulfate
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customThe crude product so obtained
  9. washwas washed with ethanol

Sources & evidence

ORD record
ord-9f16f478769448b1975ecd0b89166eed
Source dataset
uspto-grants-1998_07
Patent number
US05786355

Reaction notes

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