Hexamethylenetetramine → 3-tert-Butyl-4-hydroxy-5-methylbenzaldehyde

HRID 1708250Notes

Reaction equation

HRID 1708250 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12])([CH3:4])[CH3:3].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12])[CH:25]=[O:26])([CH3:1])[CH3:3]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 166782-tert-Butyl-6-methylphenol

Product 1

HCID 124679863-tert-Butyl-4-hydroxy-5-methylbenzaldehyde

Procedure

Under a nitrogen atmosphere, 76.65 g of 2-(1,1-dimethylethyl)-6-methylphenol (Aldrich), 65.42 g of hexamethylenetetramine and 700 ml of trifluoroacetic acid were stirred at reflux temperature for about 24 hours, then allowed to cool and evaporated. The residue from the evaporation was taken up in 1500 ml of water and 1000 ml of chloroform and neutralized to pH 7 with solid sodium carbonate. The resultant layers were separated and the aqueous layer was washed with chloroform. The organic layer was dried over sodium sulfate overnight, after which it was again washed with a volume of chloroform and evaporated. The resultant residue was then taken up in 375 ml of toluene, heated on a steam bath and then allowed to cool to room temperature overnight. Subsequent workup gave 28.3 g of the desired subtitled intermediate.

Workup

  1. temperatureat reflux temperature for about 24 hours
  2. temperatureto cool
  3. customevaporated
  4. customThe residue from the evaporation
  5. customThe resultant layers were separated
  6. washthe aqueous layer was washed with chloroform
  7. dry with materialThe organic layer was dried over sodium sulfate overnight
  8. washafter which it was again washed with a volume of chloroform
  9. customevaporated
  10. temperatureheated on a steam bath

Sources & evidence

ORD record
ord-d64abc4ac6a14a8da06484ef070d7cc7
Source dataset
uspto-grants-1994_10
Patent number
US05356917

Reaction notes

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