Ethanol → 4-(10-Bromodecyloxy)-4'-dodecylazobenzene

HRID 5753

Reaction equation

HRID 5753 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[N:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][Br:27].[OH-:28].[K+].[CH2:30](O)[CH3:31]>>[Br:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][O:28][C:6]1[CH:5]=[CH:4][C:3]([N:8]=[N:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:30][CH3:31])=[CH:12][CH:11]=2)=[CH:2][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 168972-(Phenylazo)phenolHCID 2214831,10-Dibromodecane

Product 1

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

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 solution was refluxed for seven hours. During the course of the reaction, a yellow precipitate formed in the reaction mixture. The reaction mixture 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. additionThe flask was charged with 4-dodecyl-4
  3. temperatureThe solution was refluxed for seven hours
  4. customDuring the course of the reaction
  5. customa yellow precipitate formed in the reaction mixture
  6. temperaturechilled in an ice-water bath

Sources & evidence

ORD record
ord-1a0b05586da349f5b4252b3b31d4054d
Source dataset
uspto-grants-1993_09
Patent number
US05246748

Linked notes

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