Nitric Acid → 2-Methoxy-1,3-dimethyl-5-nitrobenzene

HRID 1488449Notes

Reaction equation

HRID 1488449 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].[N+:11]([O-])([OH:13])=[O:12]>>[CH3:1][C:2]1[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 660882,6-Dimethylanisole

Product 1

HCID 1398352-Methoxy-1,3-dimethyl-5-nitrobenzeneYield 62%

Procedure

2,6-Dimethylanisole (2, 36 g, 260 mmol) was added dropwise over 0.5 h to stirred cold cone. nitric acid (200 mL) contained in round-bottom flask; stirring at room temperature was continued for 18 h. The mixture was poured onto crushed ice contained in a 1-L beaker. The resulting bright yellow solid was vacuum-filtered and dried. Recrystallization from ethanol-water gave 2,6-dimethyl-4-nitroanisole (3, 29 g, 62% yield) as a pale yellow solid, mp 90°-91° C. (lit.: Burton, G. W.; Joyce, A.; Ingold, K. U. Arch. Biochem. Biophys., 1982, 221, 281; 89°-91° C.).

Workup

  1. stirringstirring at room temperature
  2. additionThe mixture was poured
  3. customonto crushed ice
  4. filtrationThe resulting bright yellow solid was vacuum-filtered
  5. customdried
  6. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-39ca7a979efc4558a5ad9b829d9b2778
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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