Triethylamine → Propionic Acid 4-phenylazo-phenyl Ester

HRID 1157065Notes

Reaction equation

HRID 1157065 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([N:7]=[N:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[CH:5][CH:6]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:26])[CH2:24][CH3:25]>CCOCC>[C:4]1([N:7]=[N:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:23](=[O:26])[CH2:24][CH3:25])=[CH:13][CH:14]=2)[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155294-HydroxyazobenzeneHCID 62324Propionyl chloride

Product 1

HCID 58912293Propionic Acid 4-phenylazo-phenyl EsterYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4-Phenylazophenol (0.25 g, 1.26 mmoles) was dissolved in ether (5-10 mL) and triethylamine (0.26 mL) was added. Then propanoyl chloride (0.14 g 1.5 mmoles) in ether (1 mL) was added dropwise at room temperature. The mixture was stirred and reaction was rapidly completed. The reaction mixture was washed with water, dilute acid and brine and dried with magnesium sulfate. The solvent was evaporated to give 0.23 g (72%) of product. 1H NMR (CDCl3) δ=1.16 (3H, t, J=7.7), 2.40 (2H, q J=7.7), 7.25 (2H, m), 7.40-7.58 (3H, m), 7.88-8.0 (4H, m) ppm.

Workup

  1. customreaction
  2. washThe reaction mixture was washed with water
  3. additiondilute acid and brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d5eca52ef81147d8b22377cb6ac8bcbf
Source dataset
uspto-grants-2010_10
Patent number
US07807075B2

Reaction notes

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