Water → 2,4-Dimethylphenyl acetate

HRID 1586350Notes

Reaction equation

HRID 1586350 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[OH:15].[C:16](Cl)(=[O:18])[CH3:17].O>ClCCl>[C:16]([O:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[CH3:7])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 77712,4-Dimethylphenol

Product 1

HCID 1366882,4-Dimethylphenyl acetateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

83 ml (1.02 mol) of pyridine are added to a solution of 120 ml (1 mol) of 2,4-dimethylphenol in 400 ml of dichloromethane cooled to 5° C. After stirring for 15 minutes and cooling the reaction mixture to -10° C., 73 ml (1.02 mol) of acetyl chloride in solution in 100 ml of dichloromethane are added dropwise. The reaction mixture is then brought to reflux for 2 hours, then cooled and treated by the addition of 200 ml of water, and then acidified to a pH of 1. The organic phase is extracted, dried over MgSO4 and filtered on a silica bed, to lead to the production of a yellow oil: 2,4-dimethylphenyl acetate: yield 98%.

Workup

  1. temperaturecooling the reaction mixture to -10° C.
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. extractionThe organic phase is extracted
  5. dry with materialdried over MgSO4
  6. filtrationfiltered on a silica bed

Sources & evidence

ORD record
ord-151fb7867d57470fbdded3dd74e488b6
Source dataset
uspto-grants-1999_08
Patent number
US05945382

Reaction notes

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