Hydrochloric Acid → 2-Chloro-1-(2,5-dimethoxyphenyl)ethanone

HRID 1532468Notes

Reaction equation

HRID 1532468 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Cl:15][CH2:16][C:17](Cl)=[O:18].Cl>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:17](=[O:18])[CH2:16][Cl:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 90161,4-DimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2736162-Chloro-1-(2,5-dimethoxyphenyl)ethanoneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a three-neck round bottom 2 liter flask, 60.0 g (0.434 mol) of 1,4-dimethoxybenzene is added. To the flask is added 300 mL dry dichloromethane to dissolve the solid. When the solution is clear, 63.7 g (0.477 mol) of anhydrous AlCl3 is added through a powder funnel and the funnel is washed with dichloromethane. The resulting solution is yellowish in color. This solution is stirred at room temperature for 5 minutes and 40.0 mL (0.50 mol) chloroacetylchloride in 5 mL dichloromethane is added dropwise (total addition time 1 hour 30 minutes) and is stirred vigorously at room temperature. The color of the solution became is orange-red and then like red wine. The solution is stirred for 4 hours after addition at room temperature and then poured in to a mixture of crushed ice and 126 mL conc. HCl and stirred for 20 minutes again. The organic phase is separated and the aqueous phase is extracted with CH2Cl2 (100 mL×3). Total dichloromethane fractions are combined and washed with H2O (100 mL×2), cold 10% aq. NaOH (200 mL×1) and H2O (100 mL×2) and dried over anhydrous sodium sulfate. The organic phase is evaporated under reduced pressure and the thick solution is cooled to room temperature yielding a yellow solid (59.0 g, yield 64%). The crude product is crystallized from methanol (m.p. 89-91° C.).

Workup

  1. dissolutionto dissolve the solid
  2. washthe funnel is washed with dichloromethane
  3. stirringis stirred vigorously at room temperature
  4. stirringThe solution is stirred for 4 hours
  5. additionafter addition at room temperature
  6. stirringstirred for 20 minutes again
  7. customThe organic phase is separated
  8. extractionthe aqueous phase is extracted with CH2Cl2 (100 mL×3)
  9. washwashed with H2O (100 mL×2), cold 10% aq. NaOH (200 mL×1) and H2O (100 mL×2)
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe organic phase is evaporated under reduced pressure
  12. temperaturethe thick solution is cooled to room temperature

Sources & evidence

ORD record
ord-b9b17ac51ded4384841cda1977b6cfb5
Source dataset
uspto-grants-2001_03
Patent number
US06201153B1

Reaction notes

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