Water → Ethyl-m-nitrocinnamate

HRID 1256080

Reaktionsgleichung

Reaktionsgleichung von HRID 1256080
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH2:12]([O:14][C:15](=[O:25])[CH2:16]P(OCC)(OCC)=O)[CH3:13].[H-].[Na+].O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:16][C:15]([O:14][CH2:12][CH3:13])=[O:25])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

Produkt 1

HCID 94827Ethyl-m-nitrocinnamateAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-nitrobenzaldehyde (49 g, 295 mmol) and (diethoxy-phosphoryl)-acetic acid ethyl ester (72.74 g, 325 mmol) in DMF (300 ml) at 0° C. was added NaH (14.2 g, 354 mmol) portionwise and stirred for 1.5 hrs at r.t. The reaction mixture was poured into water to give colorless crystals, which were collected by filtration and washed with water and hexane to give the product ethyl 3-(3-nitrophenyl)acrylate (63 g, yield 96.6%). 1H NMR MeOD 400 MHz. δ 8.42-7.62 (m, 4H), 7.74-7.70 (d, 1H), 6.68-6.64 (d, 1H), 4.28-4.22 (m, 2H), 1.34-1.30 (m, 3H).

Aufarbeitung

  1. customto give colorless crystals, which
  2. filtrationwere collected by filtration
  3. washwashed with water and hexane

Quellen und Nachweise

ORD-Eintrag
ord-bd0fdc0f03f3443c8d05728335aaed51
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461134B2

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