Hydrochloric Acid → HCID 18385797, compound

HRID 2298332Notes

Reaction equation

HRID 2298332 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].[Cl-].[Al+3].[Cl-].[Cl-].[C:14]1([CH2:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([C:21](=[O:22])[CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[CH:4][C:3]=1[S:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 27373632-Chlorophenyl methyl sulfideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18385797HCID 18385797, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-chlorothioanisole (3.0 g) in 120 ml dichloromethane, were added slowly first 2.8 g of aluminum chloride and 3.0 g of phenylacetyl chloride at 0° C. The reaction mixture was stirred at the temperature for 12 hours. Then the reaction solution was poured onto ice and aqueous hydrochloric acid. The quenched solution was stirred for 30 minutes and extracted with dichloromethane (80 ml×3). The organic layer was washed with brine and was dried over anhydrous magnesium sulfate. After the magnesium sulfate was removed by filtration, the filtrate was concentrated in vacuo. The resulting residue was recrystallized from hexane and dichloromethane to give 3.6 g of 1-{3-chloro-4-(methylthio)phenyl}-2-phenyl-ethanone. mp: 101-102° C. NMR: δ2.51 (s, 3H), 4.22 (s, 2H), 7.17 (d, J=8.4 Hz, 1H), 7.25 (m, 3H), 7.32 (m, 2H), 7.87 (J=8.4, 1.8 Hz, 1H), 7.97 (d, J 1.8 Hz, 1H).

Workup

  1. stirringThe quenched solution was stirred for 30 minutes
  2. extractionextracted with dichloromethane (80 ml×3)
  3. washThe organic layer was washed with brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customAfter the magnesium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resulting residue was recrystallized from hexane and dichloromethane

Sources & evidence

ORD record
ord-3e933d1bf5434ce1858c714b85a8a34c
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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