Hydrochloric Acid → 2,4-Di-tert-butyl-6-hydroxybenzaldehyde

HRID 1173303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173303
Cl.N[CH2:3][C:4]1[C:9]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:8][C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][C:5]=1[OH:18].C1N2CN3CN(C2)CN1C3.[OH2:29].Cl>C(O)(=O)C.O>[C:10]([C:9]1[CH:8]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=[C:5]([OH:18])[C:4]=1[CH:3]=[O:29])([CH3:13])([CH3:12])[CH3:11]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4101HexamethylenetetramineHCID 452597712-(Aminomethyl)-3,5-di-tert-butylphenol hydrochloride

Produkt 1

HCID 128155852,4-Di-tert-butyl-6-hydroxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 1.25 g (4.60 mmol) of the product of Example 19 (as the hydrochloride salt) in 10 mL of acetic acid-water (11:3) was added 0.75 g (5.35 mmol) of hexamethylenetetramine. The mixture was refluxed for 3 h then treated with 6 mL of water and 3 mL of conc. hydrochloric acid. Heating was continued for 10 min at which point the reaction mixture was cooled and concentrated in vacuo to remove the acetic acid. The residue was partitioned between EtOAc and water, and the aqueous layer was separated and extracted. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The product was purified on a silica gel flash chromatography column eluted with 5% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h
  2. temperatureHeating
  3. temperaturewas cooled
  4. concentrationconcentrated in vacuo
  5. customto remove the acetic acid
  6. customThe residue was partitioned between EtOAc and water
  7. customthe aqueous layer was separated
  8. extractionextracted
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated
  13. customThe product was purified on a silica gel flash chromatography column
  14. washeluted with 5% EtOAc-hexane
  15. customEvaporation of the purified fractions
  16. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c194a89b6aab43b8b77c11710021fb20
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834062B2

Notizen zur Reaktion

Wird geladen…