Potassium Hydroxide → HCID 54174755, compound

HRID 1977191Notes

Reaction equation

HRID 1977191 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:15]C(=O)CC)(=[O:14])[CH2:12][CH3:13].C([O-])(=O)CC.[Na+].[OH-].[K+]>O>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[C:12]([CH3:13])[C:11]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 31263Propionic anhydrideHCID 737702,4-DifluorobenzaldehydeHCID 2723816Sodium Propionate

Product 1

HCID 54174755HCID 54174755, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml., three-necked flask is fitted with reflux condenser, drying tube, stirrer and N2 inlet. To a mixture of 55.4 g. (0.39 mole) of 2,4-difluorobenzaldehyde and 56 ml. of propionic anhydride is added 38 g. (0.39 mole) of sodium propionate. The reaction mixture is heated at 135-140° (oil bath temp.) for 19 hours with stirring under nitrogen. The still warm solution is poured into 1 l. of water with stirring. A solid separates, which upon adding 56 g. of potassium hydroxide, dissolves. The solution is extracted with ether, and then heated on the steam bath to remove the ether. After cooling in an ice-bath, concentrated hydrochloric acid is added with stirring. The product which separates is collected and washed with cold water. After drying at 60° over KOH, 2,4-difluoro-α-methylcinnamic acid, M.P. 126-128° is obtained.

Workup

  1. custom, three-necked flask is fitted
  2. temperaturewith reflux condenser
  3. customdrying tube, stirrer and N2 inlet
  4. additionTo a mixture of 55.4 g
  5. temperatureThe reaction mixture is heated at 135-140° (oil bath temp.) for 19 hours
  6. additionThe still warm solution is poured into 1 l
  7. additionA solid separates, which upon adding 56 g
  8. extractionThe solution is extracted with ether
  9. temperatureheated on the steam bath
  10. customto remove the ether
  11. temperatureAfter cooling in an ice-bath
  12. additionconcentrated hydrochloric acid is added
  13. stirringwith stirring
  14. customThe product which separates is collected
  15. washwashed with cold water
  16. dry with materialAfter drying at 60° over KOH, 2,4-difluoro-α-methylcinnamic acid
  17. customM.P. 126-128° is obtained

Sources & evidence

ORD record
ord-dfd51832d9c24e97b10d94a3769bb236
Source dataset
uspto-grants-2001_05
Patent number
US06232312B1

Reaction notes

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