Sodium Carbonate → Tert-butyl 2-nitrobenzoate

HRID 2289800Notes

Reaction equation

HRID 2289800 reaction equation
NC1C=CC=CC=1C([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=O.[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21])([O-:17])=[O:16].C([O-])([O-])=O.[Na+].[Na+]>CC(O)(C)C>[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:21])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 118752-Nitrobenzoyl chlorideHCID 3430448tert-Butyl 2-aminobenzoate

Product 1

HCID 4860715Tert-butyl 2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

t-Butyl 2-aminobenzoate ##STR103## A mixture of 2-nitrobenzoyl chloride (15 mL, 110 mmol) and t-BuOH (100 mL) were heated at reflux for 3 h. The cooled mixture was poured onto ice-water, basified with Na2CO3 and extracted with CH2Cl2 (×2). The combined organic extracts were washed with brine, the solvents evaporated in vacuo and the residue was purified by column chromatography upon silica gel using hexanes-EtOAc (95:5) as eluant to give t-butyl 2-nitrobenzoate (4.9 g, 22 mmol) as a yellow oil.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 3 h
  3. additionThe cooled mixture was poured onto ice-water
  4. extractionextracted with CH2Cl2 (×2)
  5. washThe combined organic extracts were washed with brine
  6. customthe solvents evaporated in vacuo
  7. customthe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-36f9f76af7564a48b209fe4bb559be05
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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