Hexamethylenetetramine → 5-tert-Butyl-2-hydroxy-3-(trifluoromethyl)benzaldehyde

HRID 1165441Notes

Reaction equation

HRID 1165441 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[OH:13].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:28](O)=[O:29]>O>[OH:13][C:4]1[C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][C:7]([C:9]([CH3:11])([CH3:12])[CH3:10])=[CH:6][C:5]=1[CH:28]=[O:29]

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 126521024-tert-Butyl-2-(trifluoromethyl)phenol

Product 1

HCID 198618175-tert-Butyl-2-hydroxy-3-(trifluoromethyl)benzaldehydeYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.41 g (15.5 mmol) of 2-trifluoromethyl-4-(1,1-dimethylethyl)phenol (see E. Stokker, et al, J. Med. Chem., 23:1414 (1980) as an example of how to obtain this material) and 2.24 g (16.0 mmol) of hexamethylenetetramine was refluxed in 30 ml of trifluroacetic acid for 5 hours. The solution was cooled to ambient temperature and diluted with 200 ml of water. The aqueous residue was extracted with hexane. The organic phase was washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was chromatographed on 100 g of silica gel using hexane as eluent. There was obtained 1.54 g (6.25 mmol, 40%) of 2-hydroxy-3-trifluromethyl-5-(1,1-dimethylethyl)benzaldehyde as a white solid; mp 56°-57.5° C.

Workup

  1. extractionThe aqueous residue was extracted with hexane
  2. washThe organic phase was washed with saturated sodium bicarbonate solution
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on 100 g of silica gel

Sources & evidence

ORD record
ord-85d5c2d3037b4d45ac87f34210199dae
Source dataset
uspto-grants-1990_03
Patent number
US04910202

Reaction notes

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