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

HRID 2291255Notes

Reaction equation

HRID 2291255 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-b81268db0d1c41e894dea065ecce2a80
Source dataset
uspto-grants-1989_01
Patent number
US04795664

Reaction notes

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