P-Cresol → 4-Methylphenyl acetate

HRID 1408669Notes

Reaction equation

HRID 1408669 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:5](=[O:7])[CH3:6])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 87974-Methylphenyl acetateYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous aluminum chloride (88 g, 0.66 mol) was suspended in methylene chloride (1500 mL), and then acetyl chloride (51.5 g, 0.66 mol) was added while stirring and cooling on ice. The mixture was stirred for 20 minutes while cooling on ice and 4-methylphenol (50 g, 0.46 mol) was added. The reaction mixture was stirred at room temperature for 1 h, and then poured into ice water slowly to quench the reaction. After extraction with ethyl acetate, the organic layer was washed with brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography to yield acetic acid 4-methyl-phenyl ester (52.6 g, 76%). 1H-NMR (CDCl3): 2.25 (s, 3H), 2.36 (s, 3H), 6.96 (d, 2H), 7.18 (d, 2H).

Workup

  1. temperaturecooling on ice
  2. stirringThe mixture was stirred for 20 minutes
  3. additionwas added
  4. stirringThe reaction mixture was stirred at room temperature for 1 h
  5. customto quench
  6. customthe reaction
  7. extractionAfter extraction with ethyl acetate
  8. washthe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationAfter distilling off the solvent under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-010df9b004a14410b3f7b120f2fd7727
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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