Acetyl chloride → 2'-CHLORO-4'-HYDROXYACETOPHENONE

HRID 920527Notes

Reaction equation

HRID 920527 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[CH:7]=[C:8]([O:12][CH3:13])[CH:9]=[CH:10][CH:11]=1.[C:14](Cl)([CH3:16])=[O:15]>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([O:12][CH3:13])[CH:9]=[CH:10][C:11]=1[C:14](=[O:15])[CH3:16]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 178333-ChloroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 112524022'-CHLORO-4'-HYDROXYACETOPHENONEYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a mixture of AlCl3 (42.08 g; 315.60 mmol) in CH2Cl2 (300 mL) was added dropwise 3-chloroanisole (22.50 g; 157.80 mmol), at −30° C. To the resulting mixture was added dropwise a solution of AcCl (10.50 mL; 147.63 mmol) in CH2Cl2 (100 mL) at such a rate to keep the temperature below −15° C. The resulting mixture was stirred for 4 hours at −10° C. Subsequently, the mixture was poured onto ice and extracted with CH2Cl2. The combined organic layers, were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O/hexanes 1:9) to afford 1-(2-chloro-4-methoxy-phenyl)-ethanone (17.68 g).

Workup

  1. customat −30° C
  2. customthe temperature below −15° C
  3. additionSubsequently, the mixture was poured onto ice
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layers, were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (SiO2, Et2O/hexanes 1:9)

Sources & evidence

ORD record
ord-1a6140baa4f54a6897e1989be57b34fe
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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