Propionic anhydride → CID 367964

HRID 1977188Notes

Reaction equation

HRID 1977188 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

Procedure

ρ-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 l. three-necked flask which had been flushed with nitrogen. The flask is heated gradually in an oil-bath to 140°. After 20 hours, the flask is cooled to 100° and poured into 8 l. of water. The precipitate is dissolved by adding potassium hydroxide (302 g.) in 2.1 of water. The aqueous solution is extracted with ether, and the ether extracts washed with potassium hydroxide solution. The combined aqueous layers are filtered, acidified with concentrated HCl, filtered and the collected solid washed with water, thereby producing ρ-fluoro-α-methylcinnamic acid which is used as obtained.

Workup

  1. customthree-necked flask which had been flushed with nitrogen
  2. temperatureThe flask is heated gradually in an oil-bath to 140°
  3. temperaturethe flask is cooled to 100°
  4. additionpoured into 8 l
  5. dissolutionThe precipitate is dissolved
  6. additionby adding potassium hydroxide (302 g.) in 2.1 of water
  7. extractionThe aqueous solution is extracted with ether
  8. washthe ether extracts washed with potassium hydroxide solution
  9. filtrationThe combined aqueous layers are filtered
  10. filtrationfiltered
  11. washthe collected solid washed with water
  12. customas obtained

Sources & evidence

ORD record
ord-2c6ff067ee8f46a7b4d34b7a17a002c5
Source dataset
uspto-grants-2001_05
Patent number
US06232312B1

Reaction notes

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