Chloromethyl Methyl Ether → HCID 11275484, compound

HRID 1897385Notes

Reaction equation

HRID 1897385 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.[CH3:14][O:15][CH2:16]Cl>CN(C=O)C.O>[CH3:14][O:15][CH2:16][O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 86632-NaphtholHCID 24758Sodium hydride

Product 1

HCID 11275484HCID 11275484, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5.0 g of NaH (208.33 mmol) in 150 mL of DMF under argon flow were added 20.0 g of solid 2-hydroxynaphthalene (138.7 mmol) at a temperature of 0° C., by small portions. The suspension was kept under stirring for 4 h at room temperature, 17.8 g of methoxymethyl chloride (221.2 mmol) were added slowly, and the reaction mixture was stirred for 10 additional hours. The reaction was carefully diluted with 1 L of water and the organic part was extracted with 3 times 50 mL of CH2Cl2. The combined organic extracts were washed twice with 500 mL of water, brine and dried over MgSO4. The solution was evaporated, dried in vacuum at a temperature of 80° C. to give 25.1 g of colorless oily product (133.3 mmol) that was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 10 additional hours
  2. extractionthe organic part was extracted with 3 times 50 mL of CH2Cl2
  3. washThe combined organic extracts were washed twice with 500 mL of water, brine
  4. dry with materialdried over MgSO4
  5. customThe solution was evaporated
  6. customdried in vacuum at a temperature of 80° C.

Sources & evidence

ORD record
ord-e2ff38fa0ffc4a45a6e8a54e3775291f
Source dataset
uspto-grants-2013_08
Patent number
US08519070B2

Reaction notes

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