Methanol → 5,5-Dichloro-2-isopropyl-4-pentenoic acid

HRID 1758968Notes

Reaction equation

HRID 1758968 reaction equation
[Cl:1][C:2]([Cl:14])=[CH:3][CH2:4][CH:5]([CH:11]([CH3:13])[CH3:12])[C:6]([O:8]CC)=[O:7].C(=O)([O-])[O-].[K+].[K+].CO>O>[Cl:1][C:2]([Cl:14])=[CH:3][CH2:4][CH:5]([CH:11]([CH3:12])[CH3:13])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 12959690Ethyl alpha-(3,3-dichloroallyl)isovalerate

Product 1

HCID 129596915,5-Dichloro-2-isopropyl-4-pentenoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 67.0 g (0.28 mol) of ethyl 5,5-dichloro-2-isopropyl-4-pentenoate, 77.35 g (0.56 mol) of anhydrous potassium carbonate, 2128 ml of methanol, and 708 ml of water was refluxed 4 days under nitrogen. The reaction mixture was then cooled to room temperature and about two-thirds of the solvent removed on the rotary evaporator. The residue was taken up in three times its volume of water, extracted twice with ether, and acidified with conc. HCl. The acidified reaction mixture was extracted into ether, the ether solution washed with water, dried (MgSO4), and removed. The residue was vacuum distilled to give 52.5 g (89% yield) of 5,5-dichloro-2-isopropyl-4-pentenoic acid, b.p. 91°-96° C./0.30 mm.

Workup

  1. temperaturewas refluxed 4 days under nitrogen
  2. customremoved on the rotary evaporator
  3. extractionextracted twice with ether
  4. customThe acidified reaction mixture
  5. extractionwas extracted into ether
  6. washthe ether solution washed with water
  7. dry with materialdried (MgSO4)
  8. customremoved
  9. distillationdistilled

Sources & evidence

ORD record
ord-07782173274747518c169839a1f7218a
Source dataset
uspto-grants-1982_07
Patent number
US04338326

Reaction notes

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