Hydrochloric Acid → 1-[4-(Methylthio)phenyl]-1-propanone

HRID 981253Notes

Reaction equation

HRID 981253 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](Cl)(=[O:12])[CH2:10][CH3:11].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC(Cl)C.O>[CH3:8][S:7][C:1]1[CH:6]=[CH:5][C:4]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7520ThioanisoleHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 8211711-[4-(Methylthio)phenyl]-1-propanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of thioanisole (5 g) and propionyl chloride (3.9 ml) in dichloroethane (80 ml) at 0° C. was added, in portions, aluminum chloride (6.4 g). The mixture was stirred overnight at room temperature. The reaction mixture was poured onto a mixture of ice and water (200 ml) and concentrated HCl (2 ml) and extracted with CH2Cl2. The combined organic layers were washed with water, dried over Na2SO4 and purified on a silica gel column (140 g) using hexane/EtOAc (10:1) as eluant to afford the title compound as a white solid, m.p. 60°-61° C.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. custompurified on a silica gel column (140 g)

Sources & evidence

ORD record
ord-eee85d8071b144b2b9dd675886115b2d
Source dataset
uspto-grants-1991_02
Patent number
US04990526

Reaction notes

Loading…