Potassium Carbonate → 4-Chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotoluene

HRID 978476

Reaktionsgleichung

Reaktionsgleichung von HRID 978476
[Cl:1][C:2]1[C:7](Cl)=[CH:6][C:5]([CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Cl:13][C:14]1[C:23]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=2[C:17]([OH:24])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:7]([O:24][C:17]2[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=3[C:14]([Cl:13])=[CH:15][CH:16]=2)=[CH:6][C:5]([CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzeneHCID 202033334-Chloro-5,6,7,8-tetrahydronaphthalen-1-ol

Produkt 1

HCID 132459894-Chloro-5-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-2-nitrotolueneAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution containing 39.96 g of 4,5-dichloro-2-nitrotoluene and 39.30 g of 4-chloro-5,6,7,8-tetrahydro-1-naphthol in 250 ml of DMF under an atmosphere of nitrogen and at room temperature was added 3.87 g of anhydrous potassium carbonate. The resulting mixture was then heated to 110° C. After 20 hrs at 110° C., the reaction mixture was cooled to room temperature. The DMF was removed in vacuo. The residue was dissolved in 500 ml of warm toluene and filtered through celite. The filter cake was thoroughly washed with toluene. The solvents from the combined filtrates were removed to afford 67.04 g of tan powder. This material was recrystallized from a hexane-ethyl acetate mixture to afford 49.46 g of the desired product as light tan crystals. mp 139°-140° C. NMR (CDCl3): 1.6-1.9 (m, 4H), 2.4-2.9 (m, 7H, contains singlet at 2.45), 6.51 (s, 1H), 6.73 (d, J-8 Hz, 1H), 7.18 (d, J=8 Hz, 1H), 8.15 (s, 1H).

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe DMF was removed in vacuo
  3. dissolutionThe residue was dissolved in 500 ml of warm toluene
  4. filtrationfiltered through celite
  5. washThe filter cake was thoroughly washed with toluene
  6. customThe solvents from the combined filtrates were removed

Quellen und Nachweise

ORD-Eintrag
ord-a95f99a248254827b47c9868e3f65e87
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04665097

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