Hexamethylenetetramine → 4-Hydroxy-3-(trifluoromethyl)benzaldehyde

HRID 902271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902271
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:24](O)=[O:25]>>[OH:9][C:4]1[CH:5]=[CH:6][C:7]([CH:24]=[O:25])=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1]

Komponenten

4

Edukt 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 679582-Trifluoromethylphenol

Produkt 1

HCID 70215934-Hydroxy-3-(trifluoromethyl)benzaldehydeAusbeute 36 %

Versuchsvorschrift

A solution of 2-trifluoromethyl phenol (5.0 g, 30.86 mmol) and hexamethylenetetramine (8.64 g, 61.72 mmol) in trifluoracetic acid (50 mL) was heated at 65° C. for 18 h. At the end of this time the solution was concentrated and diluted with a 2N aqueious solution of hydrochloric acid. The acid phase was extracted twice with ethyl acetate and the combined organic extract dried over magnesium sulfate and concentrated. The residue was subjected to chromatography via Biotage (FLASH 40 M, silica, 20% ethyl acetate/hexane) to yield 2.1 g (36%) of 4-hydroxy-3-(trifluoromethyl)benzaldehyde. MS (ES) m/z 188.9; HRMS: calcd for C8H5F3O2, 190.0242; found (ESI, [M+H]+), 191.0324.

Aufarbeitung

  1. concentrationAt the end of this time the solution was concentrated
  2. additiondiluted with a 2N aqueious solution of hydrochloric acid
  3. extractionThe acid phase was extracted twice with ethyl acetate
  4. extractionthe combined organic extract
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5df318bd0b38459e913645bc8fccd510
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365076B2

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