Toluene → Benzoic acid, 4-nitro-, 2-ethylhexyl ester

HRID 2245200

Reaktionsgleichung

Reaktionsgleichung von HRID 2245200
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([CH:15]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][OH:17])[CH3:14].C(N(CC)CC)C.C1(C)C=CC=CC=1>CN(C)C1C=CN=CC=1.C(OCC)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:17][CH2:16][CH:15]([CH2:13][CH3:14])[CH2:18][CH2:19][CH2:20][CH3:21])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 77202-EthylhexanolHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chloride

Produkt 1

HCID 591313Benzoic acid, 4-nitro-, 2-ethylhexyl esterAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a flask equipped with a magnetic stirrer, reflux condenser, and a nitrogen inlet was added 4-nitrobenzoyl chloride (53.0 grams, 0.285 moles), 2-ethylhexanol (28.6 grams, 0.22 moles), triethyl amine (30.2 grams, 0.30 moles) and 4-dimethylaminopyridine (6.98 grams, 0.0.57 moles) and anhydrous toluene (420 ml). The contents of the flask were heated at reflux for 16 hours; cooled to room temperature. It was diluted with diethyl ether (300 ml). The ether extract was washed with diluted HCl(1wt %, 3×100 ml), followed with a saturated sodium bicarbonate solution (3×100 ml), brine (3×100 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 57.2 grams of crude product as a yellow oil. 1H NMR (CDCl3) δ 8.3(d, 2H), 8.2(d, 2H), 4.3(d, 2H), 1.75(heptet, 1H), 1.2-1.6(m, 8H), 0.8-1.0(m, 6H).

Aufarbeitung

  1. customTo a flask equipped with a magnetic stirrer
  2. temperaturereflux condenser, and a nitrogen inlet
  3. temperatureThe contents of the flask were heated
  4. temperatureat reflux for 16 hours
  5. extractionThe ether extract
  6. washwas washed with diluted HCl(1wt %, 3×100 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f324792090394e4d94ac9dabb39d0d9a
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683017B2

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