Hydrochloric Acid → 2-Cyclopentyl-1-(2,3-dichloro-4-methoxyphenyl)ethanone

HRID 596992Notes

Reaction equation

HRID 596992 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH:11]1([CH2:16][C:17](Cl)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[Cl:8][C:7]1[C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=[CH:5][C:6]=1[C:17](=[O:18])[CH2:16][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 3485182Cyclopentylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 123955472-Cyclopentyl-1-(2,3-dichloro-4-methoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dichloroanisole (57.8 g., 0.327 mole) is dissolved in dichloromethane (300 ml.) and cyclopentylacetyl chloride (52.7 g., 0.367 mole) is added. The solution is cooled to +5° C. and aluminum chloride (48.0 g., 0.36 mole) is added gradually over a one-hour period at +5° C. The mixture is stirred for 2 hours at +5° C. and at 20°-25° C. for 16 hours and then poured into 1 liter of ice water containing 150 ml. of 12N hydrochloric acid. The organic phase is separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with sodium chloride solution, 10% sodium hydroxide and again with sodium chloride solution and dried over magnesium sulfate. On evaporation of the solvent a brown solid is obtained which is crystallized from hexane to obtain 53.2 of 2',3'-dichloro-4'-methoxy-2-cyclopentylacetophenone, m.p. 60°-61.5° C.

Workup

  1. temperatureThe solution is cooled to +5° C.
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. washThe combined organic phases are washed with sodium chloride solution, 10% sodium hydroxide and again with sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customOn evaporation of the solvent a brown solid
  7. customis obtained which
  8. customis crystallized from hexane

Sources & evidence

ORD record
ord-3659cf38a10241f39aad57388444bf23
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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