18-Crown-6 → 4-(6-Hydroxyhexyloxy)-4'-nitrobiphenyl

HRID 34691

Reaktionsgleichung

Reaktionsgleichung von HRID 34691
[K].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.I[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[OH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 2855718-Crown-6HCID 1380784-Hydroxy-4'-nitrobiphenylHCID 5462222Potassium2×HCID 130890816-Iodo-1-hexanol

Produkt 1

HCID 197795694-(6-Hydroxyhexyloxy)-4'-nitrobiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 500 ml of toluene in a one liter round bottom flask, fitted with a condenser and magnetic stirrer, are added 7.6 g (0.03M) of the potassium salt of 4-hydroxy-4'-nitrobiphenyl, 4.9 g (0.035M) of 6-iodo-1-hexanol, and 0.5 g of 18-crown-6 ether. The mixture is refluxed for about 20 hours until all of the potassium salt has dissolved and reacted as evidenced by the absence of the blue crystalline solid. The solution is filtered hot, and then cooled to room temperature. After solvent removal, the solid residue is recrystallized from ethanol to yield a purified product, m.p. 117°-119° C.

Aufarbeitung

  1. dissolutionhas dissolved
  2. customreacted
  3. filtrationThe solution is filtered hot
  4. customAfter solvent removal
  5. customthe solid residue is recrystallized from ethanol
  6. customto yield a purified product, m.p. 117°-119° C.

Quellen und Nachweise

ORD-Eintrag
ord-02e1617427244d3da1d77f0ba23e6e35
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762912

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