Chloromethyl Methyl Ether → 2,4-Dimethoxy-1-(methoxymethoxy)benzene

HRID 24703Notes

Reaction equation

HRID 24703 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[OH:17].[CH3:18][O:19][CH2:20]Cl>CC(C)=O>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][C:10]([O:17][CH2:18][O:19][CH3:20])=[C:9]([O:8][CH3:7])[CH:14]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl Ether2×HCID 11430Potassium CarbonateHCID 5930062,4-Dimethoxyphenol

Product 1

HCID 134955302,4-Dimethoxy-1-(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To anhydrous K2CO3 (3.55 g) in acetone (10 mL) under N2 was added 2,4-dimethoxyphenol (3.3 g, J.O.C. 1984, 49, 4740) in acetone (20 mL). Chloromethyl methyl ether (1.79 mL) was added dropwise and the mixture was stirred at room temperature for 18 h then heated to 50° C. for 24 h. Additional quantity of chloromethyl methyl ether (1.79 mL) was added and the mixture was stirred for another day at 50° C. and evaporated. The residue was taken up with water and extracted with AcOEt. The extract was dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane/AcOEt 20:1 to 10:1) to give 1,3-dimethoxy-4-methoxymethoxybenzene (1.18 g).

Workup

  1. temperaturethen heated to 50° C. for 24 h
  2. stirringthe mixture was stirred for another day at 50° C.
  3. customevaporated
  4. extractionextracted with AcOEt
  5. dry with materialThe extract was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel; eluent: hexane/AcOEt 20:1 to 10:1)

Sources & evidence

ORD record
ord-3b90eb9cabe84ecf9eb1344dc1055dcb
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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