Hydrochloric Acid → HCID 12395546, compound

HRID 1679710Notes

Reaction equation

HRID 1679710 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:16])[CH2:12][CH:13]([CH3:15])[CH3:14].[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:16])[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 66054Isovaleryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12395546HCID 12395546, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A stirred mixture of 2,3-dichloroanisole (265 g., 1.50 mole) and isovaleryl chloride (200 g., 1.64 mole) in methylene chloride (1.2 l.) is cooled to 5° C. and treated with aluminum chloride (220 g., 1.64 mole) during a 2-hour period. The reaction is allowed to warm to 25° C. and after 24 hours is poured into ice water (3 l.) and hydrochloric acid (600 ml.). The organic phase is washed with 10% sodium hydroxide and water and dried over magnesium sulfate. After evaporation of the solvent, the product is crystallized from hexane affording 295 g. of 2',3'-dichloro-4'-methoxyisovalerophenone which melts at 49°-54° C.

Workup

  1. temperatureto warm to 25° C. and after 24 hours
  2. washThe organic phase is washed with 10% sodium hydroxide and water
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe product is crystallized from hexane affording 295 g

Sources & evidence

ORD record
ord-82c9f1bc386548aaba8c3b6e0c9b9f62
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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