4-Ethoxyphenol → Methyl 3,5-dinitro4-(4-ethoxyphenoxy)benzoate

HRID 564840

Reaktionsgleichung

Reaktionsgleichung von HRID 564840
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH2:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[CH3:19].[OH-].[K+]>C(Cl)Cl>[N+:15]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=1[O:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:18][CH3:19])=[CH:22][CH:23]=1)[C:6]([O:8][CH3:9])=[O:7])([O-:17])=[O:16]

Komponenten

5

Edukt 3

HCID 121504-EthoxyphenolHCID 14797Potassium HydroxideHCID 96161Methyl 4-chloro-3,5-dinitrobenzoate

Produkt 1

HCID 15462359Methyl 3,5-dinitro4-(4-ethoxyphenoxy)benzoateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 13 g (50 mmole) of methyl 4-chloro-3,5-dinitrobenzoate, 7.45 g (54 mmole) of 4-ethoxyphenol, and 13 ml of potassium hydroxide solution (3.03 g, 54 mmole) was heated under argon at 150° C. for 4 h. The mixture was cooled and partitioned between 130 ml of 2 N sodium hydroxide solution and 400 ml of dichloromethane. The organic layer was washed with 2×100 ml of saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated under high vacuum to give 14.5 g, which was chromatographed on a silica gel column (5 cm×50 cm), eluting with 25% hexane/75% dichloromethane to give 13.2 g (74% yield). TLC (silica gel, CH2Cl2), Rf0.80. NMR: 1H (300 MHz) (CDCl3) 1.39 (3H, t, —CH3); 3.97 (2H, q, —CH2—); 4.02 (3H, s, —OCH3); 6.81 (4H, s, arom); and 8.70 ppm (2H, s, arom).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompartitioned between 130 ml of 2 N sodium hydroxide solution and 400 ml of dichloromethane
  3. washThe organic layer was washed with 2×100 ml of saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under high vacuum
  6. customto give 14.5 g, which
  7. customwas chromatographed on a silica gel column (5 cm×50 cm)
  8. washeluting with 25% hexane/75% dichloromethane
  9. customto give 13.2 g (74% yield)

Quellen und Nachweise

ORD-Eintrag
ord-fecbf7bc60ad4590ae6e67f6ca22c7cb
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169104A

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