Hydrochloric Acid → HCID 22616847, compound

HRID 843218Notes

Reaction equation

HRID 843218 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]=[N:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22616834HCID 22616834, compound

Product 1

HCID 22616847HCID 22616847, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

6.92 g (0.019 mol) of ethyl 6-[4-(4-cyanophenylazo)phenoxy]-hexanoate was dissolved in 250 mL of dimethylformamide in a 500 mL one-neck round flask fitted with a magnetic stirring bar and a reflux condenser by heating to 90° C. while stirring on an oil bath. 7.48 g (0.187 mol) of NaOH in 80 mL of water was added through the condenser: Stirring and heating were continued for 4 h. After cooling on an ice-water bath 40 mL of 8N HCl was added. The precipitated crude product was recovered by filtration. The precipitate was washed with 200 mL of hot ethanol. After vacuum drying at 50° C. for 20 h. 4.67 g (yield 72%) of 6-[4-(4-cyanophenylazo)phenoxy]-hexanoic acid was obtained.

Workup

  1. customfitted with a magnetic stirring bar and a reflux condenser
  2. stirringStirring
  3. temperatureheating
  4. additionwas added
  5. customThe precipitated crude product
  6. filtrationwas recovered by filtration
  7. washThe precipitate was washed with 200 mL of hot ethanol
  8. customAfter vacuum drying at 50° C. for 20 h

Sources & evidence

ORD record
ord-e2e2dd8ad0b948f89b84bc2ba9314da7
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

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