6-Chloro-1-hexanol → Bis[6-chlorohexyl]2,2 bis(4-nitrobenzyl)malonate

HRID 2246020Notes

Reaction equation

HRID 2246020 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][C:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)([C:14]([O:16][CH3:17])=[O:15])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]CO>C1(C)C=CC=CC=1.CCO.CCO.CCO.CCO.[Ti]>[Cl:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:17][O:16][C:14](=[O:15])[C:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:29][CH:28]=1)[C:10]([O:12][CH2:13][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][Cl:30])=[O:11]

Participants

5

Reactant 2

HCID 748286-Chloro-1-hexanolHCID 59217458Dimethyl bis(4-nitrobenzyl)malonate

Product 1

HCID 59217445Bis[6-chlorohexyl]2,2 bis(4-nitrobenzyl)malonateYield 69.4%

Reagents, catalysts & solvents 2

HCID 2724286Titanium(IV)ethoxideCatalystHCID 1140TolueneSolvent

Procedure

26.1 g (0.065 mol) dimethyl bis(4-nitrobenzyl)malonate, 84 g (0.61 mol) 6-chlorohexanol, 23.0 g (0.10 mol) tetraethyl orthotitanate were suspended in 50 ml toluene. The reaction mixture was subsequently allowed to react for 72 h at refluxing temperature. The reaction mixture was partitioned between water and ethyl acetate; the organic phase was washed repeatedly with water, dried over magnesium sulphate, filtered and concentrated by rotary evaporation. The product was precipitated with 200 ml cyclohexane, collected by filtration and washed with hexane to yield 27.6 g of bis[6-chlorohexyl]2,2 bis(4-nitrobenzyl)malonate as beige powder.

Workup

  1. customto react for 72 h
  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 sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe product was precipitated with 200 ml cyclohexane
  9. filtrationcollected by filtration
  10. washwashed with hexane

Sources & evidence

ORD record
ord-f4a120d244f148a2aaff8c1bd387858d
Source dataset
uspto-grants-2010_03
Patent number
US07687118B2

Reaction notes

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