Toluene → Ethyl 4-nitrobenzoate

HRID 1534152Notes

Reaction equation

HRID 1534152 reaction equation
[C:1]1(C)C=CC=C[CH:2]=1.[N+:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)([O-:10])=[O:9]>O.FC(F)C(F)(F)S(O)(=O)=O.C(O)C>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][CH2:1][CH3:2])=[O:16])=[CH:18][CH:19]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 1140TolueneHCID 61084-Nitrobenzoic Acid

Product 1

HCID 7457Ethyl 4-nitrobenzoateYield 90%

Reagents, catalysts & solvents 2

HCID 21655684HCID 21655684, compoundCatalystHCID 702EthanolSolvent

Procedure

700 g of toluene, 190 g of ethanol, 350 g of 4-nitrobenzoic acid and 7 g of tetrafluoroethanesulfonic acid hydrate are weighed into a 2-1 four-necked flask equipped as described in Example 1. The procedure described in Example 1 is then repeated. Using the work-up described in Example 1 gives 368 g of ethyl 4-nitrobenzoate and, after drying, 361 g of dry ethyl 4-nitrobenzoate, which corresponds to a yield of 88.3% of theory, in a purity of 98.9% by HPLC.

Workup

  1. customequipped

Sources & evidence

ORD record
ord-c6d299f6253449b1bdcda273d3fafb64
Source dataset
uspto-grants-1992_02
Patent number
US05087725

Reaction notes

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