Water → Tert-butyl 2-ethoxy-4-nitrobenzoate

HRID 714852Notes

Reaction equation

HRID 714852 reaction equation
[OH:1][C:2]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].I[CH2:25][CH3:26].O>CC(C)=O>[CH2:25]([O:1][C:2]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 716010782-Hydroxy-4-nitro-benzoic acid tert-butyl ester

Product 1

HCID 117840120Tert-butyl 2-ethoxy-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of tert-butyl 2-hydroxy-4-nitrobenzoate (500 mg) obtained in Step A of Example 139 in acetone (5.0 mL) were added potassium carbonate (580 mg) and iodoethane (340 μL), and the mixture was stirred overnight with heating under reflux. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (550 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cfa068110885410d8b52cbccf6c4c9bb
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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