3-Hydroxybenzaldehyde → HCID 21071449, compound

HRID 1371953Notes

Reaction equation

HRID 1371953 reaction equation
[F:1][C:2]([F:19])([CH:16]([F:18])[F:17])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1C)S([O-])(=O)=O.[OH:20][C:21]1C=C(C=CC=1)C=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:19][C:2]([F:1])([CH:16]([F:17])[F:18])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[CH:21]=[O:20]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 21071450HCID 21071450, compound

Product 1

HCID 21071449HCID 21071449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
92 °C

Procedure

Combine 3-(2,2,3,3-tetrafluoropropoxy)tosylate (200 g, 0.664 mol), 3-hydroxybenzaldehyde (101.7 g, 0.833 mol), dimethylformamide (1.5 L) and powdered potassium carbonate (192 g). Heat under stirring at 92° C. for about 22 h. Cool the reaction mixture to 40° C., pour over ice-water and extract with ethyl acetate. Combine organic phases, wash with 1 N sodium hydroxide (1 L and 0.5 L) and then a solution of saturated sodium hydrogen carbonate, dry over magnesium sulfate, filter, evaporate to dryness to provide a oily residue. Distill the oily residue under reduced pressure in a Claisen flask to give a first fraction of the title compound: bp 108–110° C. under 0.4–0.5 mmHg and a second fraction at 110–111° C. under 0.4–0.5 mmHg.

Workup

  1. temperatureHeat
  2. temperatureCool the reaction mixture to 40° C.
  3. extractionextract with ethyl acetate
  4. washCombine organic phases, wash with 1 N sodium hydroxide (1 L and 0.5 L)
  5. dry with materiala solution of saturated sodium hydrogen carbonate, dry over magnesium sulfate
  6. filtrationfilter
  7. customevaporate to dryness
  8. customto provide a oily residue
  9. distillationDistill the oily residue under reduced pressure in a Claisen flask

Sources & evidence

ORD record
ord-cf3e7ae91a2548bea3523914e14542fa
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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