4-Hydroxy-3-(trifluoromethoxy)benzaldehyde → HCID 58182218, compound

HRID 2093648Notes

Reaction equation

HRID 2093648 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].CC(C)=[O:17].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:17])=[O:7])=[CH:4][C:3]=1[O:10][C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 2

HCID 70180504-Hydroxy-3-(trifluoromethoxy)benzaldehydeHCID 131709961Jones' reagent

Product 1

HCID 58182218HCID 58182218, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 0° C. solution of 4-hydroxy-3-(trifluoromethoxy)benzaldehyde (901 mg, 4.37 mmol) in acetone (10 ml) was added 4 ml of the Jones reagent. The ice bath was removed and the reaction was stirred at room temperature for ca. 1 h. Isopropanol was added to destroy the excess Jones reagent. The mixture was diluted with ethyl acetate, the precipitate was filtered off, and the filtrate concentrated in vacuo. The residue was diluted with 1M HCl and extracted 3 times with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford the title compound. Mass spectrum (ESI) 221.1 (M−1).

Workup

  1. customThe ice bath was removed
  2. additionIsopropanol was added
  3. customto destroy the excess Jones reagent
  4. additionThe mixture was diluted with ethyl acetate
  5. filtrationthe precipitate was filtered off
  6. concentrationthe filtrate concentrated in vacuo
  7. additionThe residue was diluted with 1M HCl
  8. extractionextracted 3 times with ethyl acetate
  9. washThe combined organics were washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61822ff9297246158a9e0b403bcda9ff
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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