Hydrochloric Acid → HCID 22616850, compound

HRID 843215Notes

Reaction equation

HRID 843215 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[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:25]=[CH:24][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22616870HCID 22616870, compound

Product 1

HCID 22616850HCID 22616850, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

6.30 g (0.019 mol) of ethyl 4-[4-(4-cyanophenylazo)phenoxy]-butyrate was dissolved in a mixture of 150 mL of dimethylformamide and 40 mL of water 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. 3.8 g (0.095 mol) of NaOH was added through the condenser. Stirring and heating were continued for 1 h after which the reaction mixture was left for cooling to room temperature. The reaction mixture was then poured onto 200 of ice and acidified with 8N HCl until pH 2. The precipitated crude product was recovered by filtration. The precipitate was washed with 100 mL of hot ethanol and left overnight. After filtration and vacuum drying at 50° C. for 22 h. 5.49 g (yield 93%) of 4-[4-(4-cyanophenylazo)phenoxy]-butanoic 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 to room temperature
  6. additionThe reaction mixture was then poured onto 200 of ice
  7. customThe precipitated crude product
  8. filtrationwas recovered by filtration
  9. washThe precipitate was washed with 100 mL of hot ethanol
  10. waitleft overnight
  11. filtrationAfter filtration and vacuum
  12. customdrying at 50° C. for 22 h

Sources & evidence

ORD record
ord-e5388ed3f56349f39c9cd3c6e45bd29a
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

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