Potassium Hydroxide → HCID 54174755, compound

HRID 1107928Notes

Reaction equation

HRID 1107928 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

Conditions

Temperature
137.5 °C

Procedure

A 500 ml, three-necked flask is fitted with a reflux condenser, drying tube, stirrer and N2 inlet. To a mixture of 55.4 g (0.39 mol) of 2,4-difluorobenzaldehyde and 56 ml of propionic anhydride is added 38 g (0.39 mol) of sodium propionate. The reaction mixture is heated at 135-140° C. (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 is dissolved by 56 g of potassium hydroxide. The solution is extracted with ether. The water phase is heated on the steam bath to remove the ether. After cooling in an ice-bath, concentrated hydrochloric acid is added with stirring. The solid which separates is collected and washed with cold water. Drying at 60° C. over KOH gives 2,4-difluoro-α-methylcinnamic acid, M.P. 126-128° C.

Workup

  1. customA 500 ml, three-necked flask is fitted with a reflux condenser
  2. customdrying tube, stirrer and N2 inlet
  3. stirringwith stirring
  4. extractionThe solution is extracted with ether
  5. temperatureThe water phase is heated on the steam bath
  6. customto remove the ether
  7. temperatureAfter cooling in an ice-bath
  8. additionconcentrated hydrochloric acid is added
  9. stirringwith stirring
  10. customThe solid which separates is collected
  11. washwashed with cold water
  12. dry with materialDrying at 60° C. over KOH

Sources & evidence

ORD record
ord-fcf7dcdf628a414fbad868a355f8071a
Source dataset
uspto-grants-2000_05
Patent number
US06063818

Reaction notes

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