Water → HCID 23442870, compound

HRID 2119700Notes

Reaction equation

HRID 2119700 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:3])[CH3:2].C1N2CN3CN(C2)CN1C3.O.FC(F)(F)[C:29](O)=[O:30]>>[C:1]([O:4][C:5]1[C:6]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:8]([OH:11])=[C:9]([CH:10]=1)[CH:29]=[O:30])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 23442872t-Butyl-4-hydroxy-phenyl acetate

Product 1

HCID 23442870HCID 23442870, compoundYield 52%

Procedure

To 6.25 g of 4-acetoxy-3-t-butylphenol dissolved in 15 ml of trifluoroacetic acid was added 4.63 g of hexamethylenetetramine and the mixture was heated under reflux for 1 hour. The reaction mixture was allowed to attain room temperature, then poured into water and extracted with ethyl acetate. The organic layers were successively washed with a 1N aqueous sodium hydroxide solution, water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 20% ethyl acetate) to give 3.68 g of 5-acetoxy-4-t-butyl-2-hydroxybenzaldehyde as a pale yellow oil (52%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customto attain room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layers were successively washed with a 1N aqueous sodium hydroxide solution, water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 20% ethyl acetate)

Sources & evidence

ORD record
ord-bc53a11e08ae4194acd514cf4b098e20
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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