4-Nitrobenzoic Acid → 2-Ethylbutyl 4-nitrobenzoate

HRID 2226082Notes

Reaction equation

HRID 2226082 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([CH:15]([CH2:18][CH3:19])[CH2:16]O)[CH3:14]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:16][CH:15]([CH2:18][CH3:19])[CH2:13][CH3:14])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 73582-Ethyl-1-butanol

Product 1

HCID 189659842-Ethylbutyl 4-nitrobenzoateYield 83.2%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 167 g of p-nitrobenzoic acid, 204 g of 2-ethyl-1-butanol and 3.5 g of p-toluenesulfonic acid is refluxed and stirred for 2 hours, separating the formed water. After that, the alcohol excess is distilled off, then the formed product is distilled at 150° C. and 0.04 mmHg, to obtain 209 g of 2-ethylbutyl p-nitrobenzoate in form of a light yellow viscous liquid.

Workup

  1. temperatureis refluxed
  2. customseparating the formed water
  3. distillationAfter that, the alcohol excess is distilled off
  4. distillationthe formed product is distilled at 150° C.

Sources & evidence

ORD record
ord-717776b60bd84538ad4ead300063ab8b
Source dataset
uspto-grants-1994_09
Patent number
US05346691

Reaction notes

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