Sulfuric Acid → 2-Propenoic acid, 3-phenyl-

HRID 1591401Notes

Reaction equation

HRID 1591401 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+].S(=O)(=O)(O)O>>[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 3

HCID 1118Sulfuric AcidHCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 14798Sodium Hydroxide

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 95.3%

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. The abovementioned aqueous solution was 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 87.1 g of cinnamic acid. The purity of cinnamic acid was 96.1%, and the contents of palladium, copper and manganese were 5 ppm or less, 260 ppm, 200 ppm, respectively.

Workup

  1. customequipped with a thermometer and a stirrer
  2. customhydrolysis
  3. temperatureThe abovementioned aqueous solution was maintained at 40° C.
  4. customto precipitate the crystals of cinnamic acid
  5. additionAfter the addition of sulfuric acid
  6. customwas lowered to 20° C.
  7. filtrationby filtering through Nutsche
  8. filtrationThe resultant filter cake
  9. washwas washed with 1000 g of water
  10. customvacuum-dried at 50° C.

Sources & evidence

ORD record
ord-8dcced3d9d9d45508d857b348cf060f6
Source dataset
uspto-grants-1993_04
Patent number
US05206430

Reaction notes

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