Water → HCID 23442868, compound

HRID 2119720Notes

Reaction equation

HRID 2119720 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[CH:15]([CH3:17])[CH3:16])(=[O:3])[CH3:2].C1N2CN3CN(C2)CN1C3.O.FC(F)(F)[C:31](O)=[O:32]>>[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[CH:15]([CH3:17])[CH3:16])[CH:31]=[O:32])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 14794455HCID 14794455, compound

Product 1

HCID 23442868HCID 23442868, compoundYield 70%

Conditions

Temperature
0 °C

Procedure

1.00 g of 4-acetoxy-3,5-diisopropylphenol and 0.71 g of hexamethylenetetramine were dissolved in 4 ml of trifluoroacetic acid and the mixture was heated under reflux for 20 minutes. The reaction solution was cooled to 0° C., then combined with water and extracted with ethyl acetate. The organic layers were washed with a saturated aqueous sodium bicarbonate solution and then saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was dissolved in 10 ml of methanol, 13 ml of 1N hydrochloric acid was added, and the solution was heated under reflux for 1.5 hours. The reaction mixture was cooled to room temperature, then 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%-10% ethyl acetate) to give 0.78 g of 5-acetoxy-2-hydroxy-4,6-diisopropylbenzaldehyde as a pale yellow oil (yield 70%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layers were washed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in 10 ml of methanol
  8. addition13 ml of 1N hydrochloric acid was added
  9. temperaturethe solution was heated
  10. temperatureunder reflux for 1.5 hours
  11. temperatureThe reaction mixture was cooled to room temperature
  12. extractionextracted with ethyl acetate
  13. washThe organic layers were washed with saturated brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated
  16. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 5%-10% ethyl acetate)

Sources & evidence

ORD record
ord-c9e5fef54aa540359ca6336e06bf83e4
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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