Chloromethyl Methyl Ether → N-[4-(Methoxymethoxy)-2-nitrophenyl]acetamide

HRID 616130Notes

Reaction equation

HRID 616130 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:21][O:22][CH2:23]Cl>CC(C)=O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:21][O:22][CH3:23])=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 4024832N-(4-hydroxy-2-nitrophenyl)acetamide

Product 1

HCID 20371082N-[4-(Methoxymethoxy)-2-nitrophenyl]acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.9 G. of 1-acetamido-4-hydroxy-2-nitrobenzene, and 10 g. anhydrous potassium carbonate were stirred at room temperature in 75 ml. acetone and treated with 5 ml. chloromethyl methyl ether over 10 minutes. After a further 10 minutes, the mixture was filtered, evaporated to dryness, and the product filtered through silica gel eluting with 1% methanol to afford 1-acetamido-4-methoxymethoxy-2-nitrobenzene.

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated to dryness
  3. filtrationthe product filtered through silica gel eluting with 1% methanol

Sources & evidence

ORD record
ord-db4a00f1eb434261b047a202bb389dbf
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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