Thioanisole → 2-Methyl-1-[4-(methylthio)phenyl]-1-propanone

HRID 565090Notes

Reaction equation

HRID 565090 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:9])[CH:6]([CH3:8])[CH3:7].[C:11]1([S:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)(Cl)Cl>[CH3:7][CH:6]([CH3:8])[C:5]([C:14]1[CH:15]=[CH:16][C:11]([S:17][CH3:18])=[CH:12][CH:13]=1)=[O:9]

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 8525392-Methyl-1-[4-(methylthio)phenyl]-1-propanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-10 °C

Procedure

To a suspension of aluminum chloride (136 g, 1.02 mol) in chloroform (1.0 L) cooled to −10° C., was added dropwise isobutyrylchloride (115 mL, 1.10 mol). Then thioanisole (100 mL, 0.85 mol) was added dropwise. Upon completion of addition the reaction was allowed to proceed at r.t. for 1.5 h. The reaction was cooled to 10° C. and quenched by addition of water (750 mL). The organic layer was separated, washed with water (2×500 mL), saturated NaHCO3 solution (2×500 mL), brine (1×500 mL), and then dried over Na2SO4. After concentration in vacuo., the resulting crude product crystallized upon standing under high vacuum for 30 min to give the title compound as a brown solid.

Workup

  1. additionUpon completion of addition the reaction
  2. temperatureThe reaction was cooled to 10° C.
  3. customquenched by addition of water (750 mL)
  4. customThe organic layer was separated
  5. washwashed with water (2×500 mL), saturated NaHCO3 solution (2×500 mL), brine (1×500 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration in vacuo
  8. custom, the resulting crude product crystallized
  9. waitupon standing under high vacuum for 30 min

Sources & evidence

ORD record
ord-91c0df1965234891b27146cf048a289d
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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