Benzene → Methyl 2-(methylthio)-2-phenylacetate

HRID 388259Notes

Reaction equation

HRID 388259 reaction equation
Cl[CH:2]([S:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:8][S:7][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 3

HCID 241BenzeneHCID 6451240Aluminum(III) ChlorideHCID 13062663Methyl chloro(methylsulfanyl)acetate

Product 1

HCID 13798623Methyl 2-(methylthio)-2-phenylacetate

Procedure

In a round-bottom glass flask equipped with a magnetic stir bar methyl 2-chloro-2-(methylthio)acetate (1.3 g, 1 equiv) was dissolved in benzene (20 mL) and aluminum chloride (3.36 g, 2.8 equiv) added in one portion and heated to reflux for 3 hours. The mixture was then cooled and washed with H2O, brine, and dried over MgSO4. The organic layer was concentrated under reduced pressure to yield a yellow oil that was used without further purification (0.56 g, 35%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. temperatureThe mixture was then cooled
  4. washwashed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customto yield a yellow oil that
  8. customwas used without further purification (0.56 g, 35%)

Sources & evidence

ORD record
ord-3c2971e8cfe243e7990bdba0c53635bf
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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