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

HRID 543510Notes

Reaction equation

HRID 543510 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 was 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. The reaction mixture was thereafter heated a total of 13 hours to 200° C. and subsequently--after cooling--poured on 1 liter of ice water. The aqueous phase was extracted three times with respectively 500 ml of methylene chloride. The combined organic extracts then were washed twice with water, dried over magnesium sulfate, concentrated on a forced circulation evaporator, and distilled under vacuum, thus isolating 53.1 g, bp13 75°-78° C.

Workup

  1. temperatureThe reaction mixture was thereafter heated a total of 13 hours to 200° C.
  2. temperaturesubsequently--after cooling
  3. extractionThe aqueous phase was extracted three times with respectively 500 ml of methylene chloride
  4. washThe combined organic extracts then were washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated on a forced circulation evaporator
  7. distillationdistilled under vacuum
  8. customthus isolating 53.1 g, bp13 75°-78° C.

Sources & evidence

ORD record
ord-5fdd580abc2a42d893b46f7edf5904e5
Source dataset
uspto-grants-1984_05
Patent number
US04446147

Reaction notes

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