Hydrochloric Acid → HCID 459042, compound

HRID 843222Notes

Reaction equation

HRID 843222 reaction equation
[C:1]1([N:7]=[N:8][C:9]2[CH:21]=[CH:20][C:12]([O:13][CH2:14][C:15]([O:17]CC)=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CN(C)C=O.O>[C:1]1([N:7]=[N:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:20][CH:21]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22616848HCID 22616848, compound

Product 1

HCID 459042HCID 459042, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3.66 g (0.013 mol) of ethyl 2-[4-(phenylazo)phenoxy]-ethanoate was dissolved in a mixture of 160 mL of dimethylformamide and 40 mL of water in a 250 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. 3.6 g (0.090 mol) of NaOH was added in once through the condenser. Stirring and heating were continued for 1.5 h after which the reaction mixture was left for cooling finally on an ice-bath. The reaction mixture was then added 38 mL of 5.5 N HCl. A yellow precipitate was recovered and 40 mL of water was added. After filtration and vacuum drying 14 h at 50° C. 2.70 g (yield 82%) of 2-[4-(phenylazo)phenoxy]-ethanoic acid was obtained.

Workup

  1. customfitted with a magnetic stirring bar and a reflux condenser
  2. stirringStirring
  3. temperatureheating
  4. waitafter which the reaction mixture was left
  5. temperaturefor cooling finally on an ice-bath
  6. customA yellow precipitate was recovered
  7. addition40 mL of water was added
  8. filtrationAfter filtration and vacuum
  9. customdrying 14 h at 50° C

Sources & evidence

ORD record
ord-06e112efb68d49d4ade41cbc1bb6b88e
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

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