Methanol → Methyl Cinnamate

HRID 1506961Notes

Reaction equation

HRID 1506961 reaction equation
[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O=P(Cl)(Cl)Cl.[CH3:17]O>>[C:1]([O:11][CH3:17])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24813Phosphorus oxychlorideHCID 444539Cinnamic Acid

Product 1

HCID 637520Methyl Cinnamate

Procedure

To a round-bottomed flask, trans-cinnamic acid (7 g, 47.25 mmol) and MeOH(70 mL) were added. POCl3 (0.43 mL, 4.73 mmol) was added dropwise. The reaction mixture was stirred under reflux for 3 h. The reaction mixture was cooled to room temperature, quenched with 1N NaOH solution. The mixture was extracted by EtOAc and washed with H2O. The aqueous layer was further extracted with EtOAc. The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under vacuum (7.1 g, 80˜95%)

Workup

  1. temperatureunder reflux for 3 h
  2. customquenched with 1N NaOH solution
  3. extractionThe mixture was extracted by EtOAc
  4. washwashed with H2O
  5. extractionThe aqueous layer was further extracted with EtOAc
  6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum (7.1 g, 80˜95%)

Sources & evidence

ORD record
ord-3fe41ad9f0464b4ab819b35aaf8b7d98
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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