Water → HCID 23442881, compound

HRID 2119727Notes

Reaction equation

HRID 2119727 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=1[C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:3])[CH3:2].C1N2CN3CN(C2)CN1C3.O.[OH-].[Na+].FC(F)(F)[C:32](O)=[O:33]>>[C:1]([O:4][C:5]1[C:6]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:8]([OH:12])=[C:9]([C:10]=1[CH3:11])[CH:32]=[O:33])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 23442895HCID 23442895, compound

Product 1

HCID 23442881HCID 23442881, compound

Conditions

Temperature
0 °C

Procedure

0.33 g of 4-acetoxy-3-t-butyl-5-methylphenol and 0.33 g of hexamethylenetetramine were dissolved in 2 ml of trifluoroacetic acid and the solution was heated under reflux for 15 minutes. After cooling to 0° C., the reaction solution was combined with water, neutralized with a 2N aqueous sodium hydroxide solution, and then extracted with ethyl acetate. The organic layers were washed with a saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was dissolved in 5 ml of methanol and heated with 3.9 ml of 1N hydrochloric acid under reflux for one hour. The reaction solution was returned to room temperature and then combined with water, and the precipitated crystal was filtered off. After drying, 0.35 g of 5-acetoxy-4-t-butyl-2-hydroxy-6-methylbenzaldehyde was obtained as a white solid (72%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 15 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layers were washed with a saturated aqueous ammonium chloride solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in 5 ml of methanol
  8. temperatureheated with 3.9 ml of 1N hydrochloric acid
  9. temperatureunder reflux for one hour
  10. customwas returned to room temperature
  11. filtrationthe precipitated crystal was filtered off
  12. customAfter drying

Sources & evidence

ORD record
ord-03373dab5eaa4f3eadf5091d22fb61de
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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