Ethanol → Ethyl 3-(2-methoxyphenyl)propanoate

HRID 2229191Notes

Reaction equation

HRID 2229191 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]([O:13][CH2:19][CH3:20])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 806523-(o-Methoxyphenyl)propionic acid

Product 1

HCID 578401Ethyl 3-(2-methoxyphenyl)propanoate

Procedure

A solution of 25.0 g (139.0 mmol) 3-(2-methoxyphenyl)propionic acid in 250 mL ethanol is treated at 0° C. with 5.0 mL concentrated sulfuric acid. The reaction mixture is heated to reflux for 2 hr. The reaction mixture is cooled to room temperature and volatiles removed by rotary evaporation. The residue is diluted with 250 mL dichloromethane, washed with 200 mL water, 200 mL sat. NaHCO3, and 200 mL brine. The resulting organic layer is dried over anhydrous Na2SO4 and the solvent removed in vacuo to yield ethyl 3-(2-methoxyphenyl)propanoate, 28 g, as a tan oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 2 hr
  3. customvolatiles removed by rotary evaporation
  4. additionThe residue is diluted with 250 mL dichloromethane
  5. washwashed with 200 mL water, 200 mL sat. NaHCO3, and 200 mL brine
  6. dry with materialThe resulting organic layer is dried over anhydrous Na2SO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e04e2475f4854a3e94c05259cc91119e
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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