Propionic anhydride → CID 367964

HRID 567188Notes

Reaction equation

HRID 567188 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:14]C(=O)CC)(=[O:13])[CH2:11][CH3:12].C([O-])(=O)CC.[Na+]>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:11]([CH3:12])[C:10]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 31263Propionic anhydrideHCID 680234-FluorobenzaldehydeHCID 2723816Sodium Propionate

Product 1

HCID 367964CID 367964

Conditions

Temperature
140 °C

Procedure

p-Fluorobenzaldehyde (200 g, 1.61 mole), propionic anhydride (3.5 g, 2.42 mole) and sodium propionate (155 g, 1.61 mole) are mixed in a 1 liter, three-necked flask flushed with nitrogen. The mixture is heated gradually in an oil-bath to 140° C. After 20 hours, the flask is cooled to 100° C. and poured into 8 liters of water. The precipitate is dissolved by adding potassium hydroxide (302 g) in 2 liters of water. The aqueous solution is extracted with ether, and the ether extracts are washed with potassium hydroxide solution. The combined aqueous layers are filtered, acidified with concentrated HCl, and filtered; and the collected solid washed with water, thereby producing p-fluoro-α-methylcinnamic acid which is used as obtained.

Workup

  1. customflushed with nitrogen
  2. temperaturethe flask is cooled to 100° C.
  3. additionpoured into 8 liters of water
  4. dissolutionThe precipitate is dissolved
  5. additionby adding potassium hydroxide (302 g) in 2 liters of water
  6. extractionThe aqueous solution is extracted with ether
  7. washthe ether extracts are washed with potassium hydroxide solution
  8. filtrationThe combined aqueous layers are filtered
  9. filtrationfiltered
  10. washand the collected solid washed with water
  11. customas obtained

Sources & evidence

ORD record
ord-42f9f29ff377486cb1c11b60429e43e5
Source dataset
uspto-grants-2001_01
Patent number
US06177471B1

Reaction notes

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