Chloromethyl Methyl Ether → HCID 14677662, compound

HRID 2073598Notes

Reaction equation

HRID 2073598 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][O:11][CH2:12]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][O:11][CH2:12][O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 113342,3-DichlorophenolHCID 11430Potassium Carbonate

Product 1

HCID 14677662HCID 14677662, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixed solution of 2,3-dichlorophenol (16.3 g, 0.10 mol), chloromethyl methyl ether (9.7 g, 0.12 mol), anhydrous potassium carbonate (27.6 g, 0.20 mol), and acetonitrile (150 ml) is stirred at a temperature between 50° C. and 60° C. for 40 minutes and evaporated under reduced pressure to remove acetonitrile. The residue is dissolved in methylene chloride, washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give 20.8 g (Yield 100%) of 2,3-dichlorophenyl methoxymethyl ether as a pale yellow oil. To a hexane solution (35 ml) of 8.12 g (0.07 mol) of N,N,N',N'-tetramethylethylenediamine is dropwise added 50 ml of 15% hexane solution of butyl lithium while being stirred at a temperature of -10° C. to 0° C. and the mixture is stirred for 15 minutes.

Workup

  1. customevaporated under reduced pressure
  2. customto remove acetonitrile
  3. dissolutionThe residue is dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7f857146af8c41739465dc759dde5251
Source dataset
uspto-grants-1990_04
Patent number
US04918206

Reaction notes

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