Tetrabutylammonium Hydroxide → HCID 22616846, compound

HRID 843225Notes

Reaction equation

HRID 843225 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[CH2:23]([N+:27]([CH2:36][CH2:37][CH2:38][CH3:39])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]=[N:10][C:11]2[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2].[CH2:36]([N+:27]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:37][CH2:38][CH3:39]

Participants

4

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 22169207HCID 22169207, compound

Product 1

HCID 22616846HCID 22616846, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

1.06 g (0.004 mol) of 2-[4-(4-cyanopbenylazo)phenoxy]-ethanoic acid was transferred to a 50 mL one-neck round flask fitted with a magnetic stirring bar and 10.4 mL of a 20% aqueous solution of tetrabutylammonium hydroxide (Merck, zur Synthese) was added and the mixture heated while stirring on an oilbath until a solution was formed The solution was cooled to approx. 30° C., 3.5 mL of methylene chloride was added and vigorously stirred. The liquids were transferred to a separating funnel with a pipette and allowed to separate. The dark red, lower methylene chloride solution was drained into a 25 mL beaker. The remaining aqueous phase was washed with additional 1.5 mL of methylene chloride which was also added the beaker. The combined methylene chloride solutions of tetrabutylammonium 2-[4-(4-cyanophenylazo)phenoxy]-ethanoate were dried with Na2SO4 for ½ h and filtered. The filtercake was further washed with 1 mL of methylene chloride and the combined tetrabutylammonium 2-[4-(4-cyanophenyl-azo)phenoxy]-ethanoate solution was diluted to 8 mL corresponding to an 0.5 M solution.

Workup

  1. customfitted with a magnetic stirring bar
  2. temperaturethe mixture heated
  3. customwas formed The solution
  4. stirringvigorously stirred
  5. customThe liquids were transferred to a separating funnel with a pipette
  6. customto separate
  7. washThe remaining aqueous phase was washed with additional 1.5 mL of methylene chloride which
  8. additionwas also added the beaker
  9. dry with materialThe combined methylene chloride solutions of tetrabutylammonium 2-[4-(4-cyanophenylazo)phenoxy]-ethanoate were dried with Na2SO4 for ½ h
  10. filtrationfiltered
  11. washThe filtercake was further washed with 1 mL of methylene chloride
  12. additionthe combined tetrabutylammonium 2-[4-(4-cyanophenyl-azo)phenoxy]-ethanoate solution was diluted to 8 mL corresponding to an 0.5 M solution

Sources & evidence

ORD record
ord-b4b9cf1363454384bb3eb5b8b5c78478
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

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