HCID 135689640, compound → HCID 20233371, compound

HRID 1075133Notes

Reaction equation

HRID 1075133 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:16][CH2:17][CH2:12][CH2:13][CH2:14][CH2:15][CH3:18])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 135689640HCID 135689640, compound

Product 1

HCID 20233371HCID 20233371, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.6 g of 4-nitro-4'-(4-hydroxyphenyl)azobenzene was suspended in 40 ml of hot ethanol, placed in a sulfonation flask and rinsed with 10 ml of ethanol. Then, 0.336 g of 1-bromoheptane, 0.260 g of potassium carbonate and a spatula tip of sodium iodide were added and the dark brown suspension was stirred under reflux for 16 hours. Since starting material was still present, on additional 0.342 g of 1-bromoheptane and 0.260 g of potassium carbonate were added and the mixture was boiled under reflux for an additional 4 hours. Subsequently, the mixture was concentrated to dryness in vacuo, suspended in 30 ml of toluene and chromatographed on silica gel with 1.0 l of toluene and 0.8 l of toluene/acetone (2%). There was thus obtained 0.276 of 4-nitro-4'-(4-heptyloxy-phenyl)azobenzene which was recrystallized from methylene chloride/hexane: m.p. 146.9°-148.2° C.; cl.p. 257.7°-258.1° C.; smectic-nematic conversion 238.2° C.; ε252 =15480, ε294 =13830, ε390 =28180.

Workup

  1. customplaced in a sulfonation flask
  2. washrinsed with 10 ml of ethanol
  3. additionThen, 0.336 g of 1-bromoheptane, 0.260 g of potassium carbonate and a spatula tip of sodium iodide were added
  4. temperatureunder reflux for 16 hours
  5. additionwere added
  6. temperatureunder reflux for an additional 4 hours
  7. concentrationSubsequently, the mixture was concentrated to dryness in vacuo
  8. customchromatographed on silica gel with 1.0 l of toluene and 0.8 l of toluene/acetone (2%)

Sources & evidence

ORD record
ord-c629b3059a1d4f0a8d718d2ec1cfc4c7
Source dataset
uspto-grants-1983_07
Patent number
US04395350

Reaction notes

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