Potassium Hydroxide → 4-(10-Bromodecyloxy)-4'-dodecylazobenzene

HRID 5754

Reaction equation

HRID 5754 reaction equation
[CH2:1]([C:13]1[CH:18]=[CH:17][C:16]([N:19]=[N:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br.[OH-].[K+]>C(O)C>[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:27][C:24]1[CH:23]=[CH:22][C:21]([N:20]=[N:19][C:16]2[CH:15]=[CH:14][C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:18][CH:17]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2214831,10-DibromodecaneHCID 1356254794-Dodecyl-4'-hydroxyazobenzene

Product 1

HCID 197929294-(10-Bromodecyloxy)-4'-dodecylazobenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 3000 ml three-necked round bottom flask was equipped with magnetic stirring, a heating mantle, a reflux condenser, and a nitrogen atmosphere. The flask was charged with 4-dodecyl-4'-hydroxyazobenzene (60.0 g, 0.164 mol), 1,10-dibromodecane, (66.95 g, 0.223 mol), potassium hydroxide (9.75 g, 0.174 mol), and ethanol (1260 ml). The stirring mixture was refluxed for seven hours. During the course of the reaction, a yellow precipitate formed in the reaction mixture. The reaction mixture then was cooled to room temperature and chilled in an ice-water bath. A crude product was isolated by suction filtration, washed with water, then with hexane. The product was recrystallized from ethyl acetate.

Workup

  1. customA 3000 ml three-necked round bottom flask was equipped with magnetic stirring
  2. temperatureThe stirring mixture was refluxed for seven hours
  3. customDuring the course of the reaction
  4. customa yellow precipitate formed in the reaction mixture
  5. temperaturechilled in an ice-water bath

Sources & evidence

ORD record
ord-45d6e0e571fe4728804424dcef92127c
Source dataset
uspto-grants-1993_09
Patent number
US05246747

Linked notes

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