Nitric Acid → 3-Hydroxy-6-nitro-4-(2-propenyl)benzylalcohol

HRID 494946Notes

Reaction equation

HRID 494946 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][CH:11]=[CH2:12])[CH2:5][OH:6].[N+:13]([O-])([OH:15])=[O:14].[OH-].[Na+]>C(O)(=O)C>[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]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 14798Sodium HydroxideHCID 576828613-Hydroxy-4-(2-propenyl)benzylalcohol

Product 1

HCID 576828183-Hydroxy-6-nitro-4-(2-propenyl)benzylalcoholYield 43.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.40 g of 3-hydroxy-4-(2-propenyl)benzylalcohol (Tetrahedron, 56 (2000), 1873) was dissolved in 70 ml of acetic acid. Thereafter, 4.14 g of concentrated nitric acid and 0.6 ml of fuming nitric acid were added to the reaction solution while cooling on ice, and the obtained mixture was stirred at the same temperature for 20 minutes. Thereafter, the reaction solution was adjusted to be pH 6 with addition of a 5 N sodium hydroxide aqueous solution, while cooling on ice. It was then extracted with ethyl acetate. The extract was washed with a saturated sodium bicarbonate aqueous solution 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 4.68 g of 3-hydroxy-6-nitro-4-(2-propenyl)benzylalcohol.

Workup

  1. temperaturewhile cooling on ice
  2. temperaturewhile cooling on ice
  3. extractionIt was then extracted with ethyl acetate
  4. washThe extract was washed with a saturated sodium bicarbonate aqueous solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was then purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2e01317765be4052a168113efe2f433d
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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