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

HRID 846234Notes

Reaction equation

HRID 846234 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].[Al+3].[Cl-].[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 mixture of thioanisole (5.0 g) and propionyl chloride (3.9 ml) at 0° C. in dichloroethane (80 ml) was added AlCl3 (6.4 g) in portions. The mixture was stirred 12 hours at ambient temperature, poured into water (200 ml) and conc. HCl (2 ml), then extracted with CH2Cl2. The extract was reduced to dryness to provide the title compound mp 60°-61° C. after purification by chromatography on silica gel.

Workup

  1. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-78d5b8b098dc4f279cc9c0013bc77c03
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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