4-Cyanophenol → HCID 22131913, compound

HRID 1856596Notes

Reaction equation

HRID 1856596 reaction equation
[Na].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)#[N:3].[CH2:11]([O:14][CH2:15]Cl)[C:12]#[CH:13]>C(C(C)=O)C>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:15][O:14][CH2:11][C:12]#[CH:13])=[CH:6][CH:5]=1)#[N:3]

Participants

5

Reactant 3

HCID 130194-CyanophenolHCID 5360545SodiumHCID 122413411-Propyne, 3-(chloromethoxy)-

Product 1

HCID 22131913HCID 22131913, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A sodium salt of p-cyanophenol(14.1 g) was dissolved in methyl ethyl ketone (20 ml), and chloromethyl 2-propynyl ether (Intermediate I-a) (10.6g, 0.1 mol) prepared in example 1 was added dropwise to the solution with stirring at room temperature. The reaction mixture was stirred for further 2 hours and the solvent was then evaporated off. The residue was extracted with toluene (30 ml) and the organic layer was washed with distilled water (20 g). The solvent was then evaporated off to obtain a crude reaction product (18.7 g). This was recrystallized from hexane (60 ml) to obtain 1-cyano-4-[(2-propynyloxy)methoxy]benzene (Intermediate II-i) (15.0 g, 79.7% yield). Its chemical purity by HPLC was 99.0%.

Workup

  1. additionwas added dropwise to the solution
  2. stirringThe reaction mixture was stirred for further 2 hours
  3. customthe solvent was then evaporated off
  4. extractionThe residue was extracted with toluene (30 ml)
  5. washthe organic layer was washed with distilled water (20 g)
  6. customThe solvent was then evaporated off
  7. customto obtain a crude
  8. customThis was recrystallized from hexane (60 ml)

Sources & evidence

ORD record
ord-ce8f885c5ad64cb5b1c7b8868711edae
Source dataset
uspto-grants-2000_11
Patent number
US06143311

Reaction notes

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