Formaldehyde → Methyl 4-(2-(hydroxyimino)ethyl)benzoate

HRID 415329

Reaktionsgleichung

Reaktionsgleichung von HRID 415329
[N+:1]([CH:4]=[CH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)([O-])=[O:2].C=O.CO.[H][H]>[Pd].O1CCCC1>[OH:2][N:1]=[CH:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 887MethanolHCID 896295Methyl 4-(2-nitroethenyl)benzoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86633099Methyl 4-(2-(hydroxyimino)ethyl)benzoateAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 4-(2-nitrovinyl)benzoate (18.6 g, 90 mmol), paraformaldehyde (3.2 g, 108 mmol) and 10% Pd/C (0.9 g) in the mixture of methanol (220 mL) and tetrahydrofuran (220 mL) was stirred at room temperature over 1 atm of hydrogen for 3 h. Then the mixture was filtered and evaporated, purified by column chromatography (silica gel, petroleum ether/ethyl acetate 15:1 to 8:1) to obtain methyl 4-(2-(hydroxyimino)ethyl)benzoate (3.6 g, yield 21%) as yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.55-3.56 (d, J=6.0 Hz, 0.5H), 3.69-3.71 (d, J=5.2 Hz, 1.5H), 3.84 (s, 3H), 6.84-6.87 (t, J=5.6 Hz, 0.75H), 7.45-7.47 (t, J=6.2 Hz, 0.25H), 7.37-7.41 (m, 2H), 7.90-7.91 (m, 2H), 10.68 (s, 0.25H), 11.14 (s, 0.75H); LC-MS (ESI) m/z: 194 (M+1)+.

Aufarbeitung

  1. filtrationThen the mixture was filtered
  2. customevaporated
  3. custompurified by column chromatography (silica gel, petroleum ether/ethyl acetate 15:1 to 8:1)

Quellen und Nachweise

ORD-Eintrag
ord-22688bed82c24f008bb6b8e7f27ae4f4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088760B2

Verknüpfte Notizen

Wird geladen…