Pyridine → (3-Methyl-4-methylsulfanylphenyl) acetate

HRID 228715

Reaction equation

HRID 228715 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].N1C=CC=CC=1.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:10][C:4]1[CH:5]=[CH:6][C:7]([S:8][CH3:9])=[C:2]([CH3:1])[CH:3]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 183913-Methyl-4-(methylthio)phenol

Product 1

HCID 268463(3-Methyl-4-methylsulfanylphenyl) acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-4-methylsulfanylphenol (1.00 g) was dissolved in dichloromethane (10 ml) to prepare a solution. Pyridine (724 mg) and acetyl chloride (615 mg) were added to the solution, and the mixture was stirred at room temperature overnight. The solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using chloroform to give 3-methyl-4-methylsulfanyl-phenyl acetate (1.00 g, yield 80%).

Workup

  1. customto prepare a solution
  2. customThe solvent was removed by distillation under the reduced pressure
  3. additionWater was then added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-42d9394878e440c794c7665cd5650fd0
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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