2-Ethylhexanol → di(2-Ethylhexyl) (2Z)-2-methyl-2-butenedioate

HRID 1397647Notes

Reaction equation

HRID 1397647 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH:4]=[C:2]1[CH3:3].[CH2:9]([CH:11]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][OH:13])[CH3:10].[C:18]1([CH3:27])[CH:23]=[CH:22][C:21](S(=O)=O)=[CH:20][CH:19]=1.[CH2:28](OC(=O)C)C>>[CH2:9]([CH:11]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][O:13][C:1](=[O:8])/[C:2](=[CH:4]\[C:5]([O:7][CH2:28][CH:21]([CH2:20][CH3:19])[CH2:22][CH2:23][CH2:18][CH3:27])=[O:6])/[CH3:3])[CH3:10]

Participants

5

Reactant 4

HCID 77202-EthylhexanolHCID 8857Ethyl AcetateHCID 12012Citraconic AnhydridesHCID 178427284HCID 178427284, compound

Product 1

HCID 86683840di(2-Ethylhexyl) (2Z)-2-methyl-2-butenedioate

Conditions

Temperature
160 °C

Procedure

10 ml of citraconic anhydride (CAS no 616-02-4) and 53 ml of 2-ethyl-hexanol (CAS no 104-76-7) and 0.3 g of p-toluenesulfonic acid monohydride (CAS n 6192-52-5) were mixed in a glass flask at room temperature. The mixture was heated to 160° C., and maintained at that temperature under stirring overnight. Thereafter the mixture was cooled and diluted with 50 ml of ethylacetate, and washed twice with 100 ml of 10% NaHCO3 solution and twice with 50 ml of water, and dried with MgSO4, and filtered. Final purification of citraconate was done by vacuum distillation.

Workup

  1. temperaturemaintained at that temperature
  2. temperatureThereafter the mixture was cooled
  3. washwashed twice with 100 ml of 10% NaHCO3 solution and twice with 50 ml of water
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customFinal purification of citraconate
  7. distillationwas done by vacuum distillation

Sources & evidence

ORD record
ord-534eb1affc51422fb62c0e8d6f83d387
Source dataset
uspto-grants-2014_12
Patent number
US08901261B2

Reaction notes

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