Ethanol → Ethyl 4-nitrobenzoate

HRID 1534153Notes

Reaction equation

HRID 1534153 reaction equation
[CH2:1](O)[CH3:2].[N+:4]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)([O-:6])=[O:5]>O.FC(F)C(F)(F)C(F)(F)S(O)(=O)=O.C1(C)C=CC=CC=1>[N+:4]([C:7]1[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:1][CH3:2])=[O:12])=[CH:14][CH:15]=1)([O-:6])=[O:5]

Participants

5

Reactant 2

HCID 702EthanolHCID 61084-Nitrobenzoic Acid

Product 1

HCID 7457Ethyl 4-nitrobenzoateYield 94.4%

Reagents, catalysts & solvents 2

HCID 21655683HCID 21655683, compoundCatalystHCID 1140TolueneSolvent

Procedure

700 g of toluene, 235 g of ethanol (5.2 mol), 350 g of 4-nitrobenzoic acid and 10 g of hexafluoropropanesulfonic 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 386 g of ethyl 4-nitrobenzoate and, after drying, 382 g of dry ethyl 4-nitrobenzoate, which corresponds to a yield of 94.4% of theory, in a purity of 99.2% by HPLC of solidification point 56° C.

Workup

  1. customequipped

Sources & evidence

ORD record
ord-5fb63744e0854f84b8a13ab2eb355b94
Source dataset
uspto-grants-1992_02
Patent number
US05087725

Reaction notes

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