Dimethyl Sulfate → 3,4-Dimethoxy-2-nitrobenzaldehyde
Reaction equation
[C:1](=[O:4])([O-])[O-].[Na+].[Na+].O[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([N+:16]([O-:18])=[O:17])[C:9]=1[O:19][CH3:20].S(OC)(OC)(=O)=O>C1(C)C=CC=CC=1>[CH3:20][O:19][C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[C:11]([CH:14]=[CH:15][C:8]=1[O:4][CH3:1])[CH:12]=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Anhydrous sodium carbonate (957 g., 9.03 moles), toluene (5 liters), 4-hydroxy-3-methoxy-2-nitrobenzaldehyde (1424 g., 7.22 moles) and dimethyl sulfate (810 ml., 8.67 moles) were refluxed for 4 hours. Toluene was removed in vacuo and the residual solid dissolved in 5 liters of ethyl acetate and 3 liters of water. The organic layer was separated, washed with 2 liters of 1 N NaOH and 6 liters of brine, decolorized with charcoal, dried over magnesium sulfate and filtered. Hexane (7.6 liters) was added slowly. After cooling in an ice bath, 1527 g. product was obtained by filtration. The crude material was recrystallized from ethanol to yield 1187 g. (78%) of the title compound as a pale yellow solid, 60°-62° C.
Workup
- customToluene was removed in vacuo
- dissolutionthe residual solid dissolved in 5 liters of ethyl acetate
- customThe organic layer was separated
- washwashed with 2 liters of 1 N NaOH and 6 liters of brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- additionHexane (7.6 liters) was added slowly
- temperatureAfter cooling in an ice bath
- customproduct was obtained by filtration
- customThe crude material was recrystallized from ethanol
- customto yield 1187 g
Sources & evidence
- ORD record
- ord-92771050920449b3bf25cd04e17ea295
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04377581
Reaction notes
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