18-Crown-6 → 6-{4-[2-(4-Nitrophenyl)ethenyl]phenoxy}hexan-1-OL

HRID 620899Notes

Reaction equation

HRID 620899 reaction equation
[K].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.I[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[OH:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 130890816-Iodo-1-hexanolHCID 679201064-Hydroxy-4'-nitrostilbene potassium salt

Product 1

HCID 539381646-{4-[2-(4-Nitrophenyl)ethenyl]phenoxy}hexan-1-OL

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, is added 14 g (0.05M) of 4-hydroxy-4'-nitrostilbene potassium salt, 14 g of 6-iodo-1-hexanol, and 0.5 g of 18-crown-6 ether. The mixture is refluxed for about 20 hours, and then the reaction medium is filtered hot, and the product crystallizes from the toluene on cooling, m.p. 154°-157° C.

Workup

  1. temperatureThe mixture is refluxed for about 20 hours
  2. filtrationthe reaction medium is filtered hot
  3. customthe product crystallizes from the toluene
  4. temperatureon cooling

Sources & evidence

ORD record
ord-dce1c50af13c4af0a40110466982ed11
Source dataset
uspto-grants-1989_04
Patent number
US04822865

Reaction notes

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