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

HRID 587816Notes

Reaction equation

HRID 587816 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.[CH2:18](O)[CH3:19]>>[CH2:18]([O:11][C:10](=[O:12])[CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)[CH3:19]

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 commercially available 3-(3-hydroxy-phenyl)-propionic acid (25 g, 150.4 mmol) in ethanol (250 mL) was added concentrated sulfuric acid (3.0 mL). The solution was heated to reflux overnight. The solvent was removed in vacuo, and the resulting oil was diluted ethyl acetate and placed in a separatory funnel. The organic portion was extracted 2× with 5% NaHCO3 and once with brine. The solution was dried (MgSO4), filtered and concentrated to a dark tan oil (30 g). This material was carried on to the next step without further purification.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed in vacuo
  4. customplaced in a separatory funnel
  5. extractionThe organic portion was extracted 2× with 5% NaHCO3
  6. dry with materialThe solution was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a dark tan oil (30 g)
  9. customThis material was carried on to the next step without further purification

Sources & evidence

ORD record
ord-44c6aa5421a54dde90ff4af35343fcce
Source dataset
uspto-grants-2016_01
Patent number
US09227914B2

Reaction notes

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