Hydrogen Peroxide → Vanillamide

HRID 603434Notes

Reaction equation

HRID 603434 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%

Procedure

Hydrogen peroxide (3% aqueous solution, 155 mL, 0.151 mol) was added to 4-hydroxy-3-methoxybenzonitrile (5.00 g, 33.52 mmol) at rt. KOH (9.78 g, 148 mmol, 85% purity, reagent grade) was added, resulting in strong gas evolution [exotherm!. The solution stirred at rt for 16 h at which time sodium sulfite (5 equiv.) were added. The reaction mixture was filtered and acidified to pH 2 with HCl (2 N aqueous solution). The aqueous phase was extracted with CH2Cl2 (10×50 mL) until no product was detected by TLC in the organic extract. The combined organic phases were dried over MgSO4, filtered, and concentrated under reduced pressure to give 4.27 g (76%) of the title compound as a pale yellow solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 9.52 (s, 1H), 7.75 (s, 1H), 7.42 (d, 1H), 7.34 (dd, 1H), 7.10 (s, 1H), 6.76 (d, 1H), 3.78 (s, 3H).

Workup

  1. customresulting in strong gas evolution [exotherm
  2. additionwere added
  3. filtrationThe reaction mixture was filtered
  4. extractionThe aqueous phase was extracted with CH2Cl2 (10×50 mL) until no product
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73f0447ff477429ead956e3a6ac1dee3
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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