Hydrochloric Acid → 2',3'-Dichloro-4'-methoxyisobutyrophenone

HRID 1283243Notes

Reaction equation

HRID 1283243 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11](Cl)(=[O:15])[CH:12]([CH3:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:8][C:7]1[C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=[CH:5][C:6]=1[C:11](=[O:15])[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 123955502',3'-Dichloro-4'-methoxyisobutyrophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A stirred mixture of 2,3-dichloroanisole (I) (100 g., 0.565 mole) and isobutyryl chloride (II) (66 g., 0.62 mole) in methylene chloride (400 ml.) is cooled to 5°C. and treated with aluminum chloride (83 g., 0.62 mole) during a 1 hour period. The reaction mixture is allowed to warm to 25°C. and after 24 hours is poured into ice water (400 ml.) and hydrochloric acid (30 ml.). The organic phase is washed with 5% sodium hydroxide, water, dried over magnesium sulfate and distilled at reduced pressure affording 68 g. of 2',3'-dichloro-4'-methoxyisobutyrophenone (III) which distills at 120°-130°C./0.5 mm.

Workup

  1. temperatureto warm to 25°C. and after 24 hours
  2. washThe organic phase is washed with 5% sodium hydroxide, water
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled at reduced pressure
  5. customaffording 68 g
  6. distillationof 2',3'-dichloro-4'-methoxyisobutyrophenone (III) which distills at 120°-130°C./0.5 mm

Sources & evidence

ORD record
ord-3b920f8e778f445d97bed55215df746e
Source dataset
uspto-grants-1976_08
Patent number
US03974212

Reaction notes

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