Ethanol → 2-Ethylhexanoate

HRID 2049921Notes

Reaction equation

HRID 2049921 reaction equation
[CH2:1]([NH:5][CH:6]([P:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])[OH:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].C[CH2:23][O-:24].[Na+].C([OH:28])C>C(C(CCCC)C([O-])=O)C.C(C(CCCC)C([O-])=O)C.[Ni+2]>[CH2:1]([NH:5][CH:6]([P:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])[O-:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].[CH2:9]([CH:10]([CH2:11][CH2:12][CH2:7][CH3:6])[C:23]([O-:24])=[O:28])[CH3:8]

Participants

6

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 20342868HCID 20342868, compound

Product 2

HCID 40723562-EthylhexanoateHCID 20342867HCID 20342867, compound

Reagents, catalysts & solvents 1

HCID 107553Nickel bis(2-ethylhexanoate)Catalyst

Procedure

30.3 g (0.1 mol) of α-(n-butylamino)benzyl-phenylphosphinic acid ##STR19## are dissolved in 400 ml of absolute ethanol and neutralised with an approx. 1.5 molar ethanolic solution of 0.1 mol of sodium ethylate. 34.5 g (0.1 mol) of nickel(II) bis (2-ethylhexanoate) are additionally dissolved in this solution and the mixture is heated at reflux temperature for 30 minutes. The solvent is then evaporated and the residue is dried for 15 hours at 80° C. under a pressure of 11 mm Hg. These instructions give a light green product of the composition XLNi (X=α-(n-butylamino)benzyl-phenylphosphinate; L=2-ethylhexanoate), which contains 4.2% of phosphorus and 9.0% of nickel and is readily soluble in ethanol, chloroform, toluene and hexane at room temperature.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux temperature for 30 minutes
  3. customThe solvent is then evaporated
  4. customthe residue is dried for 15 hours at 80° C. under a pressure of 11 mm Hg

Sources & evidence

ORD record
ord-7317c4fb611447159b2d2791dba1240a
Source dataset
uspto-grants-1980_04
Patent number
US04199494

Reaction notes

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