Chloromethyl Methyl Ether → HCID 19022304, compound

HRID 257670Notes

Reaction equation

HRID 257670 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([OH:18])=[CH:15][CH:14]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21][O:22]CCl>CN(C)C=O>[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([OH:18])=[C:15]([O:22][CH3:21])[CH:14]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 19022350HCID 19022350, compound

Product 1

HCID 19022304HCID 19022304, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 g of 8-benzyl-1-naphthol was dissolved in 300 ml of N,N-dimethylformamide to give a solution. 18.6 g of sodium hydride (55% suspension in oil) was added to the solution under cooling with ice. After 30 minutes, 34.4 g of chloromethyl methyl ether was added to the obtained mixture under cooling with ice, followed by stirring for 10 minutes. The obtained mixture was further stirred at room temperature for 30 minutes. The resulting reaction mixture was poured onto ice-water and the obtained mixture was extracted with 1.2 l of ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The obtained residue was purified by silica gel column chromatography (developer: hexane to 9% ethyl acetate/hexane) to give 103 g of the title compound as a yellow oil.

Workup

  1. customto give a solution
  2. temperatureunder cooling with ice
  3. temperatureunder cooling with ice
  4. stirringThe obtained mixture was further stirred at room temperature for 30 minutes
  5. customThe resulting reaction mixture
  6. additionwas poured onto ice-water
  7. extractionthe obtained mixture was extracted with 1.2 l of ethyl acetate
  8. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in a vacuum
  11. customThe obtained residue was purified by silica gel column chromatography (developer: hexane to 9% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2a6580ed709a4648a89b42504c6ac2a7
Source dataset
uspto-grants-1993_11
Patent number
US05262565

Reaction notes

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