Acetyl chloride → 1-(3-Ethyl-4-hydroxyphenyl)ethan-1-one

HRID 396836Notes

Reaction equation

HRID 396836 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:14](Cl)(=[O:16])[CH3:15]>C(=S)=S>[CH2:1]([C:3]1[CH:8]=[C:7]([C:14](=[O:16])[CH3:15])[CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 69972-EthylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137241431-(3-Ethyl-4-hydroxyphenyl)ethan-1-oneYield 53%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred solution of 2-ethylphenol (13 g, 106.4 mmol) in carbon disulfide (30 ml) was added aluminum chloride (30 g, 225 mmol) portionwise at 0° C. Then, acetyl chloride (8.4 ml, 118.1 mmol) was added, and the mixture was heated at reflux temperature for 16 hours. The reaction mixture was cooled down to room temperature, and poured into ice. The whole was extracted with diethyl ether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was recystallized with hexane-toluene to give title compound (9.24 g, 53% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 16 hours
  3. additionpoured into ice
  4. extractionThe whole was extracted with diethyl ether
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31df67c1863d4d3e9bbd99d118b2faf5
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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