4-Hydroxybenzaldehyde → 4-(2,2,3,3-Tetrafluoropropoxy)benzaldehyde

HRID 1601372Notes

Reaction equation

HRID 1601372 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[H][H].C1(C)C=CC(S(O[CH2:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])(=O)=O)=CC=1>CCCCCC.CN(C)C(=O)C.C1C=CC=CC=1.CCCCCC>[F:29][C:25]([F:30])([CH:26]([F:28])[F:27])[CH2:24][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 20605972,2,3,3-Tetrafluoropropyl 4-toluenesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 117466214-(2,2,3,3-Tetrafluoropropoxy)benzaldehydeYield 96.1%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 31374DimethylacetamideSolventHCID 110624Benzene hexaneSolvent

Conditions

Temperature
120 °C

Procedure

After 1.90 g (43.5 mmol) of 55% sodium hydride were washed with hexane, it was suspended in 25 ml of N,N-dimethylacetamide and 5.3 g (43 mmol) of 4-hydroxybenzaldehyde were gradually added to the suspension at 0° C. under nitrogen atmosphere. When generation of hydrogen gas stopped, 11.14 g (39 mmol) of 2,2,3,3-tetrafluoropropyl p-toluenesulfonate were added to the reaction mixture, followed by heating of the resulting mixture at 120° C. with stirring for 2 hours and 15 minutes. After the reaction mixture was cooled, a mixed solvent of benzene-hexane (1:1) was added thereto and the resulting mixture was washed with water. After drying, the solvent was distilled off to obtain 8.85 g (yield: 96%) of the title compound as an oil.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. washthe resulting mixture was washed with water
  3. customAfter drying
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-57b03cdd06d94fb38255e88f14723977
Source dataset
uspto-grants-1999_11
Patent number
US05977152

Reaction notes

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