Ethanol → Ethyl 4-methoxyphenylacetate

HRID 1634631Notes

Reaction equation

HRID 1634631 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH2:13](O)[CH3:14]>S(=O)(=O)(O)O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 76904-Methoxyphenylacetic Acid

Product 1

HCID 84174Ethyl 4-methoxyphenylacetateYield 89.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
78 °C

Procedure

10 g (0.06 mol) of p-methoxyphenylacetic acid, 30 ml (0.74 mol) of ethanol and 0.11 ml (0.0026 mol) of sulfuric acid were mixed in a 250 ml balloon flask provided with thermometer and reflux cooler. The thus obtained solution was heated to reflux (78° C.) and held for 1 hour 20 minutes. It was then cooled down at room temperature and 50 ml of deionized water were added. The ethanol was evaporated under vacuum and 40 ml of dichloromethane were added over the residual aqueous phase. The thus obtained mixture was stirred and allowed to decant. The organic phase was washed with 30 ml of a sodium bicarbonate saturated solution, was dried and filtered under vacuum. After evaporating the dichloromethane under vacuum, a colorless residue of ethyl p-methoxyphenylacetate weighing 10.41 g was obtained (Yield: 89%)

Workup

  1. customprovided with thermometer
  2. temperaturereflux cooler
  3. temperatureThe thus obtained solution was heated
  4. temperatureIt was then cooled down at room temperature
  5. customThe ethanol was evaporated under vacuum and 40 ml of dichloromethane
  6. additionwere added over the residual aqueous phase
  7. customto decant
  8. washThe organic phase was washed with 30 ml of a sodium bicarbonate saturated solution
  9. customwas dried
  10. filtrationfiltered under vacuum
  11. customAfter evaporating the dichloromethane under vacuum

Sources & evidence

ORD record
ord-0f5dbb6931144eb4af75d9e98818afcb
Source dataset
uspto-grants-2003_01
Patent number
US06506941B1

Reaction notes

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