Carbon Dioxide → 4-Nitrobenzoic Acid

HRID 1641603Notes

Reaction equation

HRID 1641603 reaction equation
ON1C(=O)CCC1=O.[N+:9]([C:12]1[CH:17]=[CH:16][C:15](C)=[CH:14][CH:13]=1)([O-:11])=[O:10].[C:19](=[O:21])=[O:20].O=O>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1)([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 977OxygenHCID 74734-NitrotolueneHCID 80170N-Hydroxysuccinimide

Product 1

HCID 61084-Nitrobenzoic AcidYield 90%

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

In this example, a solution of 0.1191 g (1.03 mmol) of N-hydroxysuccinimide, 0.5104 g (3.72 mmol) of p-nitrotoluene and 0.1330 g (0.53 mmol) of cobalt acetate tetrahydrate in 40 ml of acetic acid was heated to 50° C. in a Parr Hastelloy reactor with temperature and pressure transducer. After the temperature reached 50° C., 745 psi of CO2 was introduced into the reactor, then 120 psi of O2 was added slowly to the reactor. The mixture was stirred under pressure for one hour at 50° C., then the pressure was released, and the mixture was cooled to room temperature. The solution was extracted with ethyl acetate then washed with a saturated NaCl solution in water and, dried over Na2SO4 to yield pure white solid p-nitrobenzoic acid (90% yield) after extraction by ethyl acetate with analyses by GC-MS and NMR.

Workup

  1. customreached 50° C.
  2. temperaturethe mixture was cooled to room temperature
  3. extractionThe solution was extracted with ethyl acetate
  4. washthen washed with a saturated NaCl solution in water
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-1cb5663a48404221b4c8a01d2b79869d
Source dataset
uspto-grants-2012_02
Patent number
US08115029B2

Reaction notes

Loading…