3-(3'-Hydroxyphenyl)propionic acid → Ethyl 3-(3-hydroxyphenyl)propanoate

HRID 2389337Notes

Reaction equation

HRID 2389337 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH3:18][CH2:19]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH2:18][CH3:19])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 913-(3'-Hydroxyphenyl)propionic acidHCID 702EthanolHCID 1118Sulfuric Acid

Product 1

HCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoate

Procedure

To a solution of 3-(3-hydroxyphenyl)propanoic acid (135 g) in EtOH (670 mL) was added concentrated H2SO4 (34.7 mL) at ambient temperature and the mixture was refluxed for 24 hours. After cooled to ambient temperature, the mixture was evaporated in vacuo. Water (400 mL) was added to the mixture and the mixture was extracted with EtOAc (600 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford ethyl 3-(3-hydroxyphenyl)propanoate (163 g) as a slightly yellow oil.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. customthe mixture was evaporated in vacuo
  3. additionWater (400 mL) was added to the mixture
  4. extractionthe mixture was extracted with EtOAc (600 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a8146807d0664be3b6502602daaa7713
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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