Propionic anhydride → CID 367964

HRID 377739

Reaction equation

HRID 377739 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 mol), propionic anhydride (3.5 g, 2.42 mol) and sodium propionate (155 g, 1.61 mol) are mixed in a nitrogen-flushed 1 l three-necked flask. The flask is heated gradually in an oil-bath to 140° C. After 20 hours, the contents are cooled to 100° C., and are poured into 8 l of water. The precipitate is dissolved by adding potassium hydroxide (302 g) in water (2 l). The aqueous solution is washed with ether, and the ether layers are re-extracted with potassium hydroxide solution. The combined aqueous layers are filtered, are acidified with concentrated HCl, and are filtered. The collected solid, p-fluoro-α-methylcinnamic acid, is washed with water, and is dried and used as obtained.

Workup

  1. customflushed 1 l three-necked flask
  2. temperaturethe contents are cooled to 100° C.
  3. additionare poured into 8 l of water
  4. dissolutionThe precipitate is dissolved
  5. additionby adding potassium hydroxide (302 g) in water (2 l)
  6. washThe aqueous solution is washed with ether
  7. extractionthe ether layers are re-extracted with potassium hydroxide solution
  8. filtrationThe combined aqueous layers are filtered
  9. filtrationare filtered
  10. washThe collected solid, p-fluoro-α-methylcinnamic acid, is washed with water
  11. customis dried
  12. customas obtained

Sources & evidence

ORD record
ord-e642dff59c424e39ab57fa83802bb7cb
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Linked notes

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