Sodium Carbonate → 4-(2,2,3,3-Tetrafluoropropoxy)benzaldehyde

HRID 866036Notes

Reaction equation

HRID 866036 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+].[F:13][C:14]([F:20])([CH3:19])[C:15]([F:18])([F:17])O.F[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1>>[F:13][C:14]([F:20])([CH:15]([F:18])[F:17])[CH2:19][O:2][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 127577241,1,2,2-Tetrafluoropropan-1-ol

Product 1

HCID 117466214-(2,2,3,3-Tetrafluoropropoxy)benzaldehydeYield 80%

Conditions

Temperature
140 °C

Procedure

138.2 g of potassium carbonate, 21.2 g of sodium carbonate, 198 g of tetrafluoropropanol and 124 g of 4-fluorobenzaldehyde are introduced at room temperature under argon protective gas and heated for 20 hours at 140° C. The boiling point of the reaction mixture is initially 125° C. As the reaction progresses, the internal temperature rises to 140° C. After 20 hours, the mixture is cooled to 25° C and filtered. This gives 229.6 g of filtrate containing 72% of 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde. The filter cake is washed 3 times using in each case 100 ml of toluene. Filtrate and toluene used for washing are collected separately. After 63.9 g of 2,2,3,3-tetrafluoropropanol have been distilled off from the filtrate, the distillation residue is combined with the toluene used for washing. After the toluene has been distilled off under atmospheric pressure, the residue is fractionated in vacuo at 3 mbar and a bottom temperature of up to 135° C. and a head temperature of 109° C. to 110° C. As the main fraction, 188.7 g of 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde with a purity (GC) of 98% to 99% are obtained.

Workup

  1. customis initially 125° C
  2. customAs the reaction progresses
  3. customrises to 140° C
  4. temperaturethe mixture is cooled to 25° C
  5. filtrationfiltered
  6. additionThis gives 229.6 g of filtrate containing 72% of 4-(2,2,3,3-tetrafluoropropoxy)benzaldehyde
  7. washThe filter cake is washed 3 times
  8. washfor washing
  9. customare collected separately
  10. distillationAfter 63.9 g of 2,2,3,3-tetrafluoropropanol have been distilled off from the filtrate
  11. washfor washing
  12. distillationAfter the toluene has been distilled off under atmospheric pressure
  13. customup to 135° C.
  14. customa head temperature of 109° C. to 110° C

Sources & evidence

ORD record
ord-3a3d3f01f7b0442e9ff8e1adb0c53aaa
Source dataset
uspto-grants-1996_10
Patent number
US05569776

Reaction notes

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