Water → Benzyl 3-benzyloxy-2-nitrobenzoate

HRID 636466Notes

Reaction equation

HRID 636466 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, wished 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. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel flash chromatography (hexane—ethyl acetate)
  5. customcrystallized with diisopropyl ether

Sources & evidence

ORD record
ord-7560fc245ee64b04816e148868022783
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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