Hexamethylenetetramine → 2-Hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde

HRID 1710000

Reaktionsgleichung

Reaktionsgleichung von HRID 1710000
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>O>[OH:12][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:6][C:5]=1[CH:25]=[O:26]

Komponenten

5

Edukt 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 134994724-tert-Butyl-3-chlorophenol

Produkt 1

HCID 230354272-Hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehydeAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 9.65 g (52.2 mmol) of 3-chloro-4-(1,1-dimethylethyl)phenol and 7.37 g (52.2 mmol) of hexamethylenetetramine was refluxed in 150 ml of trifluoroacetic acid for 3 hours. The solution was cooled to ambient temperature and diluted with 500 ml of water. The aqueous residue was extracted with ether. The organic phase was washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was chromatographed on 250 g of silica gel using a gradient from hexane to 20:80 (v/v) ether: hexane as eluent. There was obtained 1.87 g (8.79 mmol, 17%) of 2-hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde; mp 38°-39° C.

Aufarbeitung

  1. extractionThe aqueous residue was extracted with ether
  2. washThe organic phase was washed with saturated sodium bicarbonate solution
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on 250 g of silica gel using a gradient from hexane to 20:80 (v/v) ether

Quellen und Nachweise

ORD-Eintrag
ord-375129a6d5c34d1b9ba00aca701d145e
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04952583

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