Potassium Iodide → Methyl 5-Benzyloxy-4-methoxy-2-nitrobenzoate

HRID 1917817Notes

Reaction equation

HRID 1917817 reaction equation
[OH:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C=O)C>[CH2:17]([O:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 53396387Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

Product 1

HCID 22667156Methyl 5-Benzyloxy-4-methoxy-2-nitrobenzoateYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
92.5 °C

Procedure

To solution of methyl 5-hydroxy-4-methoxy-2-nitrobenzoate (13.0 g, 0.0572 mol) in DMF (120 mL) and benzyl chloride (7.23 ml, 0.0629 mol), K2CO3 (8.69 g, 0.0629 mol) and potassium iodide (0.949 g, 0.0057 mol) were added. The reaction mixture was heated at 90-95° C. overnight. The solvent was evaporated under vacuum and the residue was taken in ethyl acetate and washed with water and brine. After drying over MgSO4, the solution was concentrated ad purified on silica gel column to yield methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate (13.99 g, 77% yield). 1HNMR (DMSO-d6): δ 7.66 (1H, s), 7.40 (6H, m), 5.27 (2H, s), 3.83 (3H, s), 3.80 (3H, s). LC-MS (ESI) m/z 318 (M+H)+.

Workup

  1. customThe solvent was evaporated under vacuum
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution was concentrated ad
  5. custompurified on silica gel column

Sources & evidence

ORD record
ord-1433d64ff88c449d9ec941759dd1a7db
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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