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

HRID 2167838Notes

Reaction equation

HRID 2167838 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-a6faafba334b4a4b8e0760fec17a6d28
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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