Propionic anhydride → CID 367964

HRID 1276393Notes

Reaction equation

HRID 1276393 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 one liter three-necked flask which had been flushed with nitrogen. The flask is heated gradually in an oil-bath to 140° C. After 20 hours, the flask is cooled to 100° C. and poured into 8 l of water. The precipitate is dissolved by adding potassium hydroxide (302 g) in 2 l 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, 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. customhad been flushed with nitrogen
  2. temperaturethe flask is cooled to 100° C.
  3. additionpoured into 8 l of water
  4. dissolutionThe precipitate is dissolved
  5. additionby adding potassium hydroxide (302 g) in 2 l 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. 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-c9f627546ee249a7801478ea636eacbd
Source dataset
uspto-grants-2000_12
Patent number
US06166053

Reaction notes

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