Water → 2,3,5-Trimethylphenyl acetate

HRID 1821689Notes

Reaction equation

HRID 1821689 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].N1C=CC=CC=1.[C:17](OC(=O)C)(=[O:19])[CH3:18].O>ClCCl>[C:17]([O:10][C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 127692,3,5-Trimethylphenol

Product 1

HCID 136963592,3,5-Trimethylphenyl acetateYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (150 mL) was dissolved 15.09 g (0.1108 mol) of 2,3,5-trimethylphenol, and 17.82 mL (0.2204 mol) of pyridine, then 20.78 mL (0.2202 mol) of acetic anhydride were added to the solution, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with dichloro-methane. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (Wako gel C-100, hexane:ethyl acetate, gradient) to obtain 20.08 g (0.1127 mol, Yield: quantitative) of 2,3,5-trimethylphenyl acetate.

Workup

  1. extractionextracted with dichloro-methane
  2. washThe organic layer was successively washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified by silica gel column chromatography (Wako gel C-100, hexane:ethyl acetate, gradient)

Sources & evidence

ORD record
ord-e3919b88346c4647b2d35ef532045225
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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