Propanedioic acid, dibutyl ester → Tetrabutyl propane-1,1,2,3-tetracarboxylate

HRID 904911Notes

Reaction equation

HRID 904911 reaction equation
[Na].[C:2]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:11])[CH2:3][C:4]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:5].[C:17]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:27])/[CH:18]=[CH:19]\[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21]>C(O)CCC.Cl>[CH:3]([C:4]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:5])([C:2]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11])[CH:18]([C:17]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])[CH2:19][C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21]

Participants

6

Reactant 3

HCID 136925Propanedioic acid, dibutyl esterHCID 5271569Dibutyl maleateHCID 5360545Sodium

Product 1

HCID 20478063Tetrabutyl propane-1,1,2,3-tetracarboxylateYield 95.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 2631-ButanolSolvent

Procedure

One half gram of sodium metal is dissolved in 200 mls n-butanol and to this solution is added 108 g (0.5 mol) of dibutyl malonate. After reacting for five minutes, 114 grams (0.5 mole) of dibutyl maleate is added and the reaction mixture is refluxed for 6 hours. The solution is neutralized with a few drops of conc. hydrochloric acid and then filtered. The excess n-butanol is distilled off in vacuo to give 213 grams of a tetrabutyl propane-1,1,2,3-tetracarboxylate. The structure is confirmed by NMR analysis (CDCl3) ##STR11##

Workup

  1. temperaturethe reaction mixture is refluxed for 6 hours
  2. filtrationfiltered
  3. distillationThe excess n-butanol is distilled off in vacuo

Sources & evidence

ORD record
ord-d0be3202cdad45fa8e969b7e93501b88
Source dataset
uspto-grants-1983_12
Patent number
US04420621

Reaction notes

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