Dimethylformamide → 1-(Benzyloxy)-2-methoxy-4-nitrobenzene

HRID 1822826Notes

Reaction equation

HRID 1822826 reaction equation
O.[K].[N+:3]([C:6]1[CH:7]=[C:8]([OH:14])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)([O-:5])=[O:4].C(Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:23]N(C)C=O>C(=O)([O-])[O-].[Cs+].[Cs+]>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][C:8]=1[O:14][CH3:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 1317257234-Nitroguaiacol potassium salt monohydrate

Product 1

HCID 217867071-(Benzyloxy)-2-methoxy-4-nitrobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 10796Cesium carbonateCatalyst

Procedure

4-Nitroguaiacol potassium salt monohydrate (25 g, 111 mmol) and cesium carbonate (3.25 g, 10 mmol) were transferred into a 500 ml one-neck flask and dry dimethylformamide (200 ml) was added, benzyl bromide (21.4 g, 125 mmol) was added dropwise at room temperature under N2 atmosphere and the reaction mixture was stirred vigorously for about 3 hours. The solvent and the excess of benzylbromide were then removed under reduced pressure. Water (200 ml) and ethanol (100 ml) was added to the crude product and refluxed for 10–15 minutes. The yellowish crystalls were filtered from the cold mixture, washed with water and dried to give 29 g (100% yield) of the title compound.

Workup

  1. customThe solvent and the excess of benzylbromide were then removed under reduced pressure
  2. additionWater (200 ml) and ethanol (100 ml) was added to the crude product
  3. temperaturerefluxed for 10–15 minutes
  4. filtrationThe yellowish crystalls were filtered from the cold mixture
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-03b9855da5ec4e54a5c4183248a0a4e0
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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