Water → Benzyl 3-benzyloxy-2-nitrobenzoate

HRID 2287542Notes

Reaction equation

HRID 2287542 reaction equation
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:20]([O:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1)=[O:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2932913-Hydroxy-2-nitrobenzoic acid

Product 1

HCID 10594871Benzyl 3-benzyloxy-2-nitrobenzoateYield 136.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-hydroxy-2-nitrobenzoic acid (500 mg) and potassium carbonate (1.13 g) in dimethylformamide (5 ml) was added benzyl bromide (1.12 g) at ambient temperature, and the mixture was stirred overnight. To the reaction mixture was added water, and extracted with ethyl acetate twice. The organic layers were combined, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel flash chromatography (hexane-ethyl acetate) and crystallized with diisopropyl ether to give benzyl 3-benzyloxy-2-nitrobenzoate (676 mg).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel flash chromatography (hexane-ethyl acetate)
  6. customcrystallized with diisopropyl ether

Sources & evidence

ORD record
ord-3c9b8fae7497413bb3ee77f3913b70f3
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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