Methyl iodide → 4-Allyl-5-methoxy-2-nitrobenzyl alcohol

HRID 494947Notes

Reaction equation

HRID 494947 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:7]([N+:13]([O-:15])=[O:14])=[CH:8][C:9]=1[CH2:10][CH:11]=[CH2:12])[CH2:5][OH:6].[C:16](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:16][O:1][C:2]1[CH:3]=[C:4]([C:7]([N+:13]([O-:15])=[O:14])=[CH:8][C:9]=1[CH2:10][CH:11]=[CH2:12])[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 576828183-Hydroxy-6-nitro-4-(2-propenyl)benzylalcohol

Product 1

HCID 576827814-Allyl-5-methoxy-2-nitrobenzyl alcoholYield 78.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.68 g of 3-hydroxy-6-nitro-4-(2-propenyl)benzylalcohol was dissolved in 90 ml of N,N-dimethylformamide. Thereafter, 3.71 g of potassium carbonate and 3.81 g of iodomethane were added to the reaction solution, and the obtained mixture was stirred at room temperature overnight. The reaction solution was extracted with ethyl acetate, and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was then purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 3.93 g of the subject compound.

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was then purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8b16132dc53240a18536984412ed64e3
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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