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

HRID 2215278Notes

Reaction equation

HRID 2215278 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.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:24](O)[CH3:25]>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH2:24][CH3:25])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 913-(3'-Hydroxyphenyl)propionic acidHCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium Carbonate

Product 1

HCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoateYield 90%

Procedure

A solution of 3-(3-hydroxyphenyl)propionic acid (Lancaster, 66.4 g, 0.4 mol) in ethanol (700 mL) was treated with concentrated sulfuric acid (6 mL), heated to reflux for 2 h, and allowed to cool to RT. The mixture was cooled in ice, neutralized with 10% aqueous sodium carbonate and concentrated in vacuo to about 50 mL. Water (˜200 mL) was added and the mixture was extracted three-times with ethyl acetate. The combined ethyl acetate extract was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to yield the title compound as an oil (70 g, 90%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. temperatureThe mixture was cooled in ice
  4. concentrationconcentrated in vacuo to about 50 mL
  5. additionWater (˜200 mL) was added
  6. extractionthe mixture was extracted three-times with ethyl acetate
  7. extractionThe combined ethyl acetate extract
  8. washwas washed with water and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27bb2ea3dc9b4de0997afb678122fd34
Source dataset
uspto-grants-2006_09
Patent number
US07109238B2

Reaction notes

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