Hexamethylenetetramine → 4-Hydroxy-3-(trifluoromethyl)benzaldehyde

HRID 1987424Notes

Reaction equation

HRID 1987424 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:24](O)=[O:25]>>[OH:9][C:4]1[CH:5]=[CH:6][C:7]([CH:24]=[O:25])=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 679582-Trifluoromethylphenol

Product 1

HCID 70215934-Hydroxy-3-(trifluoromethyl)benzaldehydeYield 36%

Procedure

A solution of 2-trifluoromethyl phenol (5.0 g, 30.86 mmol) and hexamethylenetetramine (8.64 g, 61.72 mmol) in trifluoracetic acid (50 mL) was heated at 65° C. for 18 h. At the end of this time the solution was concentrated and diluted with a 2N aqueious solution of hydrochloric acid. The acid phase was extracted twice with ethyl acetate and the combined organic extract dried over magnesium sulfate and concentrated. The residue was subjected to chromatography via Biotage (FLASH 40 M, silica, 20% ethyl acetate/hexane) to yield 2.1 g (36%) of 4-hydroxy-3-(trifluoromethyl)benzaldehyde. MS (ES) m/z 188.9; HRMS: calcd for C8H5F3O2, 190.0242. found (ESI, [M+H]+), 191.0324.

Workup

  1. concentrationAt the end of this time the solution was concentrated
  2. additiondiluted with a 2N aqueious solution of hydrochloric acid
  3. extractionThe acid phase was extracted twice with ethyl acetate
  4. extractionthe combined organic extract
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c6fe0d21ce549deab84d62f11fb4266
Source dataset
uspto-grants-2009_06
Patent number
US07550485B2

Reaction notes

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