Ethanol → Ethyl (4-chlorophenyl)acetate

HRID 1364409Notes

Reaction equation

HRID 1364409 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 84177Ethyl (4-chlorophenyl)acetate

Procedure

4-Chlorophenyl acetic acid (5.0 g; 29.3 mmol) is dissolved in 50 mL absolute ethanol. With stirring, 100 μL sulfuric acid is added to the solution and the reaction is heated to reflux for 2 hours. The ethanol is removed by rotary evaporation and the resulting oil is dissolved in ethyl acetate. The organics are washed successively with saturated sodium bicarbonate, water, and brine, then dried over magnesium sulfate. After removing the ethyl acetate by rotary evaporation, the resulting oil is dried under vacuum at 35° C. for two hours to give 5.60 grams of 4-chlorophenylacetic acid ethyl ester.

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 2 hours
  3. customThe ethanol is removed by rotary evaporation
  4. dissolutionthe resulting oil is dissolved in ethyl acetate
  5. washThe organics are washed successively with saturated sodium bicarbonate, water, and brine
  6. dry with materialdried over magnesium sulfate
  7. customAfter removing the ethyl acetate
  8. customby rotary evaporation
  9. customthe resulting oil is dried under vacuum at 35° C. for two hours

Sources & evidence

ORD record
ord-21decddfbfce4fbdbb220c8a6a8c6ff4
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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