Water → 2,5-Dimethyl-4-hexenoic Acid Ethyl Ester

HRID 371450Notes

Reaction equation

HRID 371450 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5](C(OCC)=O)([CH3:11])[CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH3:2].[Cl-].[Li+].O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH3:11])[CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 13080719Diethyl methyl(3-methylbut-2-en-1-yl)propanedioate

Product 1

HCID 130807222,5-Dimethyl-4-hexenoic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

85.3 g of 2-ethoxycarbonyl-2,5-dimethyl-4-hexenoic acid ethyl ester is dissolved in 645 ml of dimethyl sulfoxide and combined in succession with 29.7 g of lithium chloride and 6.3 ml of distilled water. Then the reaction mixture is heated for a total of 13 hours to 200° C. and then--after having been allowed to cool down--is poured on 1 liter of ice water. The aqueous phase is extracted three times with respectively 500 ml of methylene chloride. The combined organic extracts are then washed twice with water, dried over magnesium sulfate, concentrated with the aid of a forced-circulation evaporator, and distilled under vacuum, thus isolating 53.1 g, bp13 75°-78° C.

Workup

  1. temperatureThen the reaction mixture is heated for a total of 13 hours to 200° C.
  2. temperatureto cool down
  3. extractionThe aqueous phase is extracted three times with respectively 500 ml of methylene chloride
  4. washThe combined organic extracts are then washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated with the aid of a forced-circulation evaporator
  7. distillationdistilled under vacuum
  8. customthus isolating 53.1 g, bp13 75°-78° C.

Sources & evidence

ORD record
ord-bf7729e90bdb4f558de6d441dee8dd49
Source dataset
uspto-grants-1985_07
Patent number
US04532236

Reaction notes

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