Hydrochloric Acid → HCID 23442860, compound

HRID 2119732Notes

Reaction equation

HRID 2119732 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([OH:14])=[CH:7][C:6]=1[C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:3])[CH3:2].C1N2CN3CN(C2)CN1C3.Cl.[C:30](OC1C(C(C)(C)C)=CC(O)=C(C=1C(C)C)C=O)(=[O:32])C>FC(F)(F)C(O)=O.O>[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([OH:14])=[C:7]([C:6]=1[C:15]([CH3:16])([CH3:17])[CH3:18])[CH:30]=[O:32])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 4101HexamethylenetetramineHCID 23442854HCID 23442854, compoundHCID 23442869HCID 23442869, compound

Product 1

HCID 23442860HCID 23442860, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

0.75 g of 4-acetoxy-3-t-butyl-5-isopropylphenol and hexamethylenetetramine were dissolved in 2.6 ml of trifluoroacetic acid and the solution was heated under reflux for 15 minutes. After cooling to 0° C., 2 ml of 3N hydrochloric acid was added and the solution was heated under reflux for 1.5 hours. Additional 2 ml of 3N hydrochloric acid was added and the solution was heated under reflux for 5 hours. After cooling to room temperature, the reaction solution was combined with water and extracted with ethyl acetate. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 5% ethyl acetate) to give 0.40 g of a mixture of 5-acetoxy-4-t-butyl-2-hydroxy-6-isopropylbenzaldehyde and 5-acetoxy-6-t-butyl-2-hydroxy-4-isopropylbenzaldehyde as a pale yellow oil (yield 48%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 15 minutes
  3. temperaturethe solution was heated
  4. temperatureunder reflux for 1.5 hours
  5. temperaturethe solution was heated
  6. temperatureunder reflux for 5 hours
  7. temperatureAfter cooling to room temperature
  8. extractionextracted with ethyl acetate
  9. washThe organic layers were washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated
  12. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 5% ethyl acetate)

Sources & evidence

ORD record
ord-890748bdab8a45a9b1142c049f0c3fb4
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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