Hydrogen Peroxide → Vanillamide

HRID 2424954Notes

Reaction equation

HRID 2424954 reaction equation
OO.[OH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][CH3:13].[OH-].[K+].S([O-])([O-])=[O:17].[Na+].[Na+]>>[OH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]([NH2:9])=[O:17])=[CH:6][C:5]=1[O:12][CH3:13]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 24437Sodium SulfiteHCID 781354-Hydroxy-3-methoxybenzonitrile

Product 1

HCID 354088VanillamideYield 76.2%

Procedure

A 3% aqueous solution of hydrogen peroxide (155 mL, 0.151 mol) was added to a flask containing 4-hydroxy-3-methoxybenzonitrile (5.00 g, 33.52 mmol) at rt. Solid KOH (9.78 g, 174.33 mmol) was added slowly. Gas was evolved and the temperature of the rose. The solution was stirred for 16 h, and excess sodium sulfite was added. The mixture was then filtered and the solution was acidified to pH 2 with 2N HCl. The aqueous solution was extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the product as a pale yellow solid (4.27 g, 76.2%). 1H NMR (400 MHz, DMSO-d6) δ 9.52 (s, 1H), 7.75 (s, 1H), 7.42 (d, 1H), 7.34 (dd, 1H), 7.096 (s, 1H), 6.76 (d, 1H), 3.78 (s, 3H).

Workup

  1. filtrationThe mixture was then filtered
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1478f54685224d81bb991e87a223fc19
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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