Methanol → HCID 12531875, compound

HRID 1863301Notes

Reaction equation

HRID 1863301 reaction equation
CO.C[O-].[Na+].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>C1C=CC=CC=1.O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 46844-ChlorophenolHCID 10942334Sodium MethoxideHCID 20392600HCID 20392600, compound

Product 1

HCID 12531875HCID 12531875, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 40 ml of methanol, 1.19 g of sodium methoxide and 3.21 g of p-chlorophenol is added 7.4 g of methyl α-bromo-α-[p-(p-cyanophenoxy)phenyl]acetate in 15 ml of benzene. The mixture is refluxed for 20 hours, poured into ice and water, and extracted with ether. The ether extracts are washed with 10% potassium carbonate and with water. Drying over magnesium sulfate and removal of the solvent under vacuum gives a tan oil. Filtration once through silica gel with chloroform as solvent gives an oil in the first fractions. The oil is filtered through silica gel with benzene as the solvent to give, in the first fractions, a pale yellow oil.

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. extractionextracted with ether
  3. washThe ether extracts are washed with 10% potassium carbonate and with water
  4. dry with materialDrying over magnesium sulfate and removal of the solvent under vacuum
  5. customgives a tan oil
  6. filtrationFiltration once through silica gel with chloroform as solvent
  7. customgives an oil in the first fractions
  8. filtrationThe oil is filtered through silica gel with benzene as the solvent
  9. customto give, in the first fractions

Sources & evidence

ORD record
ord-2479370bafc846609b8060e1f540962f
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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