2-Propenoic acid, 3-phenyl-, methyl ester → 2-Propenoic acid, 3-phenyl-

HRID 1591402Notes

Reaction equation

HRID 1591402 reaction equation
[C:1]([O:11]C)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([OH:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 14798Sodium Hydroxide

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 95.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

100 g of crude methyl cinnamate and 926.8 g of 2.8% caustic soda were placed in a 2-liter flask equipped with a thermometer and a stirrer, and the solution was then stirred at 80° C. for 30 minutes to carry out hydrolysis. An active carbon treatment was omitted. Then, 100 g of toluene was added to this aqueous solution, followed by stirring at 80° C. for 30 minutes. After the stop of the stirring, the solution was allowed to stand and separate and the resultant toluene layer was then removed. The resultant aqueous layer was placed in a 2-liter flask equipped with a thermometer and a stirrer and then maintained at 40° C., and 137.1 g of 25% sulfuric acid was added dropwise to precipitate the crystals of cinnamic acid. After the addition of sulfuric acid had been over, the temperature of the solution was lowered to 20° C., followed by filtering through Nutsche. The resultant filter cake was washed with 1000 g of water, and then vacuum-dried at 50° C. to obtain 87.6 g of cinnamic acid. The purity of cinnamic acid was 97.4%, and the contents of palladium, copper and manganese were 5 ppm or less, 290 ppm, 240 ppm, respectively.

Workup

  1. customequipped with a thermometer and a stirrer
  2. customhydrolysis
  3. stirringby stirring at 80° C. for 30 minutes
  4. customseparate
  5. customthe resultant toluene layer was then removed
  6. customThe resultant aqueous layer was placed in a 2-liter flask
  7. customequipped with a thermometer and a stirrer
  8. temperaturemaintained at 40° C.
  9. addition137.1 g of 25% sulfuric acid was added dropwise
  10. customto precipitate the crystals of cinnamic acid
  11. additionAfter the addition of sulfuric acid
  12. customwas lowered to 20° C.
  13. filtrationby filtering through Nutsche
  14. filtrationThe resultant filter cake
  15. washwas washed with 1000 g of water
  16. customvacuum-dried at 50° C.

Sources & evidence

ORD record
ord-1bfd138890b84fa8b49c24317878ec4a
Source dataset
uspto-grants-1993_04
Patent number
US05206430

Reaction notes

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