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Pyridine → 3,5-Dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester

HRID 1250801
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1250801
[CH3:1][O:2][C:3](=[O:22])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[C:8]([O:20][CH3:21])[CH:7]=1.[N+:23]([C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([N+:35]([O-:37])=[O:36])[CH:34]=1)[C:29](Cl)=[O:30])([O-:25])=[O:24].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CC=CN=1)C>[C:3]([O-:22])(=[O:2])[CH3:4].[CH3:21][O:20][C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([O:2][CH3:1])=[O:22])[CH:11]=[CH:10][C:9]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:29](=[O:30])[C:28]1[CH:27]=[C:26]([N+:23]([O-:25])=[O:24])[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 74323,5-Dinitrobenzoyl chlorideHCID 541470624-(6-Hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester

Produkt 2

HCID 175AcetateHCID 543196263,5-Dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl esterAusbeute 176,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 218852-DimethylaminopyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.50 g (8.11 mmol) of 4-(6-hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester, 1.96 g (8.51 mmol) of 3,5-dinitrobenzoyl chloride and 10 mg (0.08 mmol) of dimethylaminopyridine were dissolved in 25 ml of methylene chloride. 3.3 ml (40.5 mmol) of pyridine were added dropwise, in the course of 20 minutes at 0° C., to the resulting clear solution. After 2 hours at 0° C. the reaction mixture was partitioned between methylene chloride and water; the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water. The organic phase was then dried over magnesium sulphate, filtered and concentrated by evaporation. Chromatography of the residue on 150 g of silica gel using toluenelethyl acetate 9:1 yielded 3.6 g of 3,5-dinitrobenzoic acid 6-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]hexyl ester.

Aufarbeitung

  1. customAfter 2 hours at 0° C. the reaction mixture was partitioned between methylene chloride and water
  2. washthe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water
  3. dry with materialThe organic phase was then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e338315390d74529a9fdeb31a01793ea
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06340506B1

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