Methanol → HCID 20392629, compound

HRID 1863312Notes

Reaction equation

HRID 1863312 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[CH3:20]O>S(Cl)(Cl)=O>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:20])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 12531840[p-(p-Cyanophenoxy)phenyl]acetic Acid

Product 1

HCID 20392629HCID 20392629, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 22.25 g of [p-(p-cyanophenoxy)phenyl]acetic acid in 55 ml of thionyl chloride is refluxed for one hour. The solvent is removed under vacuum, benzene is added (three times) and the solvent removed under vacuum. The residue is dissolved in 135 ml of methanol and stirred at room temperature for 1 hour. The solvent is removed under vacuum to give a gum. The gum is dissolved in 50 ml of warm methanol and the solution is chilled and filtered to give the product, mp 58°-60° C.

Workup

  1. customThe solvent is removed under vacuum, benzene
  2. additionis added (three times)
  3. customthe solvent removed under vacuum
  4. dissolutionThe residue is dissolved in 135 ml of methanol
  5. customThe solvent is removed under vacuum
  6. customto give a gum
  7. temperaturethe solution is chilled
  8. filtrationfiltered
  9. customto give the product, mp 58°-60° C.

Sources & evidence

ORD record
ord-71c85e1da45d4ab282ab97331515b219
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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