Chloromethyl Methyl Ether → HCID 20095706, compound

HRID 1770236Notes

Reaction equation

HRID 1770236 reaction equation
[Br:1][C:2]1[C:3]([O:15][CH2:16][CH3:17])=[C:4](OC)[C:5]([O:10][CH2:11][CH3:12])=[C:6]([OH:9])[C:7]=1[CH3:8].[H-].[Na+].[CH3:20][O:21][CH2:22]Cl>CN(C=O)C>[Br:1][C:2]1[C:3]([O:15][CH2:16][CH3:17])=[CH:4][C:5]([O:10][CH2:11][CH3:12])=[C:6]([O:9][CH2:20][O:21][CH3:22])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 20095710HCID 20095710, compound

Product 1

HCID 20095706HCID 20095706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

54 g of 5-bromo-2,4-diethoxy-3-methoxy-6-methylphenol prepared in Referential Example 7 was dissolved in 250 ml of DMF, and 8.5 g of sodium hydride (55% oil suspension) was added thereto and cooled by ice while stirring. The mixture was stirred at room temperature for 30 min and cooled again with ice, and 17.1 g of methoxymethyl chloride was dropwise added thereto. After the completion of the dropwise addition, the mixture was further stirred at room temperature for 30 min. Ice water was added thereto, and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate, concentrated and purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=95:5) to prepare 43.6 g of the product compound as a colorless oleaginous substance.

Workup

  1. temperaturecooled by ice
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. additionwas dropwise added
  4. additionAfter the completion of the dropwise addition
  5. stirringthe mixture was further stirred at room temperature for 30 min
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. custompurified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=95:5)
  11. customto prepare 43.6 g of the product compound as a colorless oleaginous substance

Sources & evidence

ORD record
ord-6d2af6704d0340c482929e73cbe231bf
Source dataset
uspto-grants-1995_01
Patent number
US05385942

Reaction notes

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