Hydrochloric Acid → 1-(4-(methylthio)phenyl)-2-phenylethanone

HRID 482911Notes

Reaction equation

HRID 482911 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([S:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:1]1([CH2:7][C:8]([C:14]2[CH:15]=[CH:16][C:11]([S:17][CH3:18])=[CH:12][CH:13]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7520ThioanisoleHCID 7679Phenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27600881-(4-(methylthio)phenyl)-2-phenylethanoneYield 898.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 46.8 g (0.030 mole) of phenylacetyl chloride in dry methylene chloride (330 ml) was added 37.6 g (0.030 mole) of thioanisole. The solution was cooled to 5° in an ice-acetone bath, and anhydrous aluminum chloride (40.9 g, 0.031 mole) was added portionwise over 30 minutes at a rate to maintain the temperature constant at 5°. The reaction mixture was stirred at 5° for 3.5 hours, after which time the mixture was carefully poured into 1300 ml of aqueous 1N HCl and was stirred overnight. The layers were separated and the aqueous layer was extracted with methylene chloride (2×1l). The organic fractions were combined and washed with 1N hydrochloric acid (2×500 ml), 5% aqueous sodium hydroxide (2×500 ml) and brine (2×500 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The crystalline product was collected by filtration and washed with cold ethanol to afford 65.3 g (89%) of 2-phenyl-1-(4-methylthiophenyl)ethanone as a white solid, m.p. 98°-100°.

Workup

  1. temperatureThe solution was cooled to 5° in an ice-acetone bath
  2. temperatureto maintain the temperature constant at 5°
  3. stirringwas stirred overnight
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with methylene chloride (2×1l)
  6. washwashed with 1N hydrochloric acid (2×500 ml), 5% aqueous sodium hydroxide (2×500 ml) and brine (2×500 ml)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. filtrationThe crystalline product was collected by filtration
  10. washwashed with cold ethanol

Sources & evidence

ORD record
ord-12376aeb9b8c44fbb57082290e972d94
Source dataset
uspto-grants-1986_03
Patent number
US04576958

Reaction notes

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