Sulfuric Acid → 6-Chlorohexyl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoate

HRID 2090147Notes

Reaction equation

HRID 2090147 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][C:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)([C:13]([OH:15])=[O:14])C(O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][CH:9]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[C:13]([O:15][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][Cl:28])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 748286-Chloro-1-hexanolHCID 229285922,2-Bis(4-nitrobenzyl)malonic acid

Product 1

HCID 593812656-Chlorohexyl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoateYield 78.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 g (2.67 mmol) of 2,2-bis(4-nitrobenzyl)malonic acid and 1.42 ml (10.7 mmol) 6-chlorohexanol were suspended in 5.0 ml toluene. 1.0 ml sulphuric acid are added. The reaction mixture was subsequently allowed to react for 21.5 hours at refluxing temperature. The reaction mixture was partitioned between water and ethyl acetate; the organic phase was washed repeatedly with water, dried over magnesium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 150 g silica gel using toluene:ethyl acetate 19:1 as eluant yielded 0.94 g (78%) 6-chlorohexyl 2-(4-nitrobenzyl)-3-(4-nitrophenyl)propanoate as yellow oil.

Workup

  1. customto react for 21.5 hours
  2. temperatureat refluxing temperature
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washthe organic phase was washed repeatedly with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-10719248b8644f75a894ff204998c733
Source dataset
uspto-grants-2013_05
Patent number
US08436132B2

Reaction notes

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