Chloromethyl Methyl Ether → HCID 21939841, compound

HRID 1242905Notes

Reaction equation

HRID 1242905 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20]Cl.[CH2:22]([CH:24]1[O:26][CH2:25]1)Br>CN(C)C=O.O>[CH3:18][O:19][CH2:20][O:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:22][CH:24]1[CH2:25][O:26]1

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 35051094-Nitrocatechol

Product 1

HCID 21939841HCID 21939841, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

1,2-Dihydroxy-4-nitrobenzene (4.65 g, 0.030 mol), potassium carbonate (8.71 g, 0.063 mol) and methoxymethyl chloride (2.42 g, 0.030 mol) were dissolved in dimethylformamide (50 ml), which was stirred at 40° C. for 30 minutes. Epibromohydrin (7.20 g, 0.045 mol) was added to the mixture, which was stirred at 60° C. for 80 minutes. Then water was added, and extraction was conducted using ethyl acetate. The organic layer was washed with water, and concentrated. The residue was purified by alumina column chromatography (development solvent: ethyl acetate-n-hexane=1:4), to give 2-[[2-(methoxymethoxy)-5-nitrophenoxy]methyl]oxirane (2.61 g) as a white powder.

Workup

  1. stirringwas stirred at 60° C. for 80 minutes
  2. extractionextraction
  3. washThe organic layer was washed with water
  4. concentrationconcentrated
  5. customThe residue was purified by alumina column chromatography (development solvent: ethyl acetate-n-hexane=1:4)

Sources & evidence

ORD record
ord-f3eadbdce3da401ca5468cc144ef2461
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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