Hydrogen Peroxide → Vanillamide
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
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
- filtrationThe mixture was then filtered
- extractionThe aqueous solution was extracted with dichloromethane
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9b32a54535ef4880b4645cc47c59622c
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592361B2
Reaction notes
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