Water → 2,3,5-Trifluoro-4-hydroxybenzaldehyde

HRID 492575Notes

Reaction equation

HRID 492575 reaction equation
[CH2:1]1N2CN3CN(C2)CN1C3.[F:11][C:12]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=1[OH:20].[OH2:21].OS(O)(=O)=O>C(O)(C(F)(F)F)=O>[F:18][C:17]1[C:12]([F:11])=[C:13]([OH:20])[C:14]([F:19])=[CH:15][C:16]=1[CH:1]=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 5179882,3,6-Trifluorophenol

Product 1

HCID 451201142,3,5-Trifluoro-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Add hexamethylenetetramine (7.10 g, 50.6 mmol) portion wise to a solution of 2,3,6-trifluorophenol (5.00 g, 33.7 mmol) in TFA (35 ml) at ambient temperature and reflux for 15 hours. After cooling, treat the reaction mixture with water (60 ml), followed by 50% aq. H2SO4 (30 ml), and stir at ambient temperature for 30 minutes. Extract with EtOAc (2×) and wash with 1N aq. HCl (3×) and water. Extract the organic with 2N aq. NaOH (2×) and acidify the alkaline extract with conc. HCl while cooling in an ice/water bath. Collect the resulting solid via filtration and dry to give 2,3,5-trifluoro-4-hydroxy-benzaldehyde (2.97 g) as an off-white solid.

Workup

  1. temperaturereflux for 15 hours
  2. temperatureAfter cooling
  3. extractionExtract with EtOAc (2×)
  4. washwash with 1N aq. HCl (3×) and water
  5. extractionExtract the organic with 2N aq. NaOH (2×)
  6. extractionextract with conc. HCl
  7. temperaturewhile cooling in an ice/water bath
  8. customCollect the resulting solid
  9. filtrationvia filtration
  10. customdry

Sources & evidence

ORD record
ord-468f9a434ca24eecb552987d9e795908
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

Loading…