Allyl bromide → 3-Allyloxy-4-methoxynitrobenzene

HRID 28456

Reaction equation

HRID 28456 reaction equation
[Na].[N+:2]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([OH:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:14](Br)[CH:15]=C.[CH2:18](Cl)Cl.CCCCCC>CN(C=O)C>[CH2:12]([O:11][C:9]1[CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=[CH:7][C:8]=1[O:13][CH3:18])[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 767382-Methoxy-4-nitrophenolHCID 5360545SodiumHCID 21226440Methylenechloride Hexane

Product 1

HCID 120822023-Allyloxy-4-methoxynitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

97.5 g (0.51 mole) of the sodium salt of 5-nitroguaiacol was dissolved in one liter of DMF and 1.5 equivalents of allyl bromide added. The reaction was heated to 65° C. for two hours, after which time much of the dark color had discharged and tlc (1:1 CH2Cl2/hexane) indicated loss of starting material. The solvent was concentrated in vacuum and the residue washed with water. The product was isolated by filtration and dried in a vacuum. This gave 112 g of pale yellow solid. A sample recrystallized from methanol, gave m.p. 93-94° C.

Workup

  1. concentrationThe solvent was concentrated in vacuum
  2. washthe residue washed with water
  3. customThe product was isolated by filtration
  4. customdried in a vacuum
  5. customA sample recrystallized from methanol
  6. customgave m.p. 93-94° C.

Sources & evidence

ORD record
ord-3f44aa63a8b8417582fb109a69f778d9
Source dataset
uspto-grants-2008_09
Patent number
US07419986B2

Linked notes

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