Hexamethylenetetramine → 5-(2,6-Dichloro-4-methoxymethyl-phenoxy)-2-methoxy-benzaldehyde

HRID 1168092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1168092
[Cl:1][C:2]1[CH:16]=[C:15]([CH2:17][O:18][CH3:19])[CH:14]=[C:13]([Cl:20])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:33](O)=[O:34].C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:16]=[C:15]([CH2:17][O:18][CH3:19])[CH:14]=[C:13]([Cl:20])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([CH:6]=1)[CH:33]=[O:34]

Komponenten

6

Edukt 4

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 222856594-(2,6-Dichloro-4-methoxymethyl-phenoxy)-anisole

Produkt 1

HCID 222856575-(2,6-Dichloro-4-methoxymethyl-phenoxy)-2-methoxy-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of the title compound of Step B (410 mg, 1.31 mmol), hexamethylenetetramine (256 mg, 2.0 mmol) and trifluoroacetic acid (2.5 ml) under nitrogen was heated to 75° C. and stirred for about three hours. The solution was concentrated in vacuo to give a yellow viscous oil. Water (20 ml) was added to the yellow oil and the mixture was stirred for about 30 minutes at room temperature. The aqueous solution was neutralized with saturated sodium bicarbonate and extracted with ethyl acetate (3×30 ml). The combined organic extracts were washed with saturated sodium bicarbonate (2×50 ml), brine (50 ml), dried, filtered and concentrated to give the title compound (440 mg ) as a crude product which was used in the next step without further purification. NMR (400 MHz, CDCl3) δ10.36 (s, 1H), 7.33 (s, 2H), 7.11-7.16 (m, 2H), 6.93 (d, 1H), 4.39 (s, 2H), 3.86 (s, 3H), 3.40 (s, 3H).

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. customto give a yellow viscous oil
  3. stirringthe mixture was stirred for about 30 minutes at room temperature
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. washThe combined organic extracts were washed with saturated sodium bicarbonate (2×50 ml), brine (50 ml)
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2ad06077ec1e4dbfb6f1d89e3b9e2508
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620830B2

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