Sodium Methoxide → HCID 14257052, compound

HRID 622069Notes

Reaction equation

HRID 622069 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[C:11](Cl)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][O-:19].[Na+]>CN(C)P(N(C)C)(N(C)C)=O>[Cl:16][C:12]1[C:13]([Cl:15])=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][C:11]=1[O:19][CH3:18]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14257051HCID 14257051, compound

Product 1

HCID 14257052HCID 14257052, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 3,4,5-trichlorophenol benzyl ether (7.5 g, 0.026 mole) and sodium methoxide (1.7 g, 0.032 mole) in hexamethylphosphoramide (60 ml) was heated with stirring on a steam bath for 20 hours. The reaction mixture was poured into ice water, extracted into ether, washed with water, brine, and dried over magnesium sulfate. The solvent was evaporated at reduced pressure and the residual oil chromatographed on silica gel (320 g) eluting with ethyl acetate-hexane; 1:4 to obtain 1.1 g of 2,3-dichloro-5-benzyloxyanisole which melted at 79°-81° C.

Workup

  1. temperaturewas heated
  2. extractionextracted into ether
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated at reduced pressure
  6. customthe residual oil chromatographed on silica gel (320 g)
  7. washeluting with ethyl acetate-hexane

Sources & evidence

ORD record
ord-5eccffeb36a44f7cbed0976622385b66
Source dataset
uspto-grants-1988_09
Patent number
US04769370

Reaction notes

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