Ethylenediaminetetraacetic Acid → 5-Butyl-4-methyldihydro-2(3H)-furanone

HRID 1915981Notes

Reaction equation

HRID 1915981 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH:9](=O)[CH2:10][CH2:11]CC.[OH-].C(C([NH+](C(CCCC)(CCCC)C)CCCCCC[NH3+])(CCCC)C)CCC.[OH-].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>O>[CH3:9][CH2:10][CH2:11][CH2:8][CH:7]1[O:6][C:1](=[O:5])[CH2:2][CH:3]1[CH3:4]

Participants

6

Reactant 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 8063PentanalHCID 429065Ethyl trans-crotonateHCID 23501653HCID 23501653, compound

Product 1

HCID 629005-Butyl-4-methyldihydro-2(3H)-furanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl crotonate (6.9% by weight) and pentanal (5.2% by weight) were emulsified in an aqueous electrolyte (0.16% by weight of bis(dibutylethyl)hexamethylenediammonium hydroxide (bisquat), 0.38% by weight of EDTA, 0.14% by weight of TEA, 1.45% by weight of Na2B4O7 and 5.84% by weight of Na2HPO4 in water at a pH of 10) (all % by weight based on the total aqueous reaction electrolyte) and subjected to galvanostatic electrolysis at a current density of 2.23 A/dm2 and a temperature of 25° C. in a frame electrolysis cell. The current throughput was 2 F/mol of ester. A steel anode and a lead cathode were used as electrodes (electrode area of 0.1 dm2 and spacing of 1 cm). To monitor the reaction, the MTBE extract of a sample of the electrolysis output is analyzed by gas chromatography. A yield of 3-methyl-4-butylbutyrolactone (whiskey lactone) of 68.5% and a yield of the corresponding ethyl γ-hydroxycarboxylate of 24.2% were achieved. This corresponded to a total yield of target products of 92.7% of the theoretical yield.

Workup

  1. customa temperature of 25° C.
  2. customthe reaction
  3. extractionthe MTBE extract of a sample of the electrolysis output

Sources & evidence

ORD record
ord-91eb2d475505449ea6aef9854fbdbfab
Source dataset
uspto-grants-2013_12
Patent number
US08617376B2

Reaction notes

Loading…