Dimethylformamide → HCID 18419367, compound

HRID 989752Notes

Reaction equation

HRID 989752 reaction equation
[Na].[N+:2]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8](O)=[CH:7][CH:6]=1)([O-:4])=[O:3].C(Br)[CH:15]=[CH2:16].C(Cl)Cl.CCCCCC.CN([CH:30]=[O:31])C>>[CH2:12]([O:11][C:9]1[C:10]([O:31][CH3:30])=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=[CH:7][CH:8]=1)[CH:15]=[CH2:16]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 767382-Methoxy-4-nitrophenolHCID 5360545SodiumHCID 21226440Methylenechloride Hexane

Product 1

HCID 18419367HCID 18419367, compound

Conditions

Temperature
65 °C

Procedure

97.5 g (0.51 mole) of the sodium salt of 5-nitroguaiacol was dissolved in one Vliter 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 tic (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. additionadded
  2. concentrationThe solvent was concentrated in vacuum
  3. washthe residue washed with water
  4. customThe product was isolated by filtration
  5. customdried in a vacuum
  6. customA sample recrystallized from methanol
  7. customgave m.p. 93-94° C.

Sources & evidence

ORD record
ord-b07b7ba8d0c942a18494b87159908af4
Source dataset
uspto-grants-2002_10
Patent number
US06458802B1

Reaction notes

Loading…