Pyridine → 4-Isopropyl-3-methylphenyl acetate

HRID 228709Notes

Reaction equation

HRID 228709 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[CH3:11])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:18](Cl)(=[O:20])[CH3:19]>ClCCl>[C:18]([O:10][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[C:5]([CH3:11])[CH:6]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 185973-Methyl-4-isopropylphenol

Product 1

HCID 232400044-Isopropyl-3-methylphenyl acetateYield 110.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Isopropyl-3-methylphenol (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, and the solvent was removed by distillation under the reduced pressure. The residue was dried under the reduced pressure to give 4-isopropyl-3-methylphenyl acetate (1.41 g, yield 100%).

Workup

  1. customto prepare a solution
  2. customThe solvent was removed by distillation under the reduced pressure, water
  3. additionwas 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 dried under the reduced pressure

Sources & evidence

ORD record
ord-68e3d250e9204389916fe0ddd9ec6858
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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