Water → 5,5-Dichloro-3-methyl-2-(propan-2-yl)pent-4-enoic acid

HRID 1758971Notes

Reaction equation

HRID 1758971 reaction equation
[Cl:1][C:2]([Cl:15])=[CH:3][CH:4]([CH3:14])[CH:5]([CH:11]([CH3:13])[CH3:12])[C:6]([O:8]CC)=[O:7].[OH-].[Na+].O>C(O)C>[Cl:1][C:2]([Cl:15])=[CH:3][CH:4]([CH3:14])[CH:5]([CH:11]([CH3:12])[CH3:13])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 12959693Ethyl 5,5-dichloro-3-methyl-2-propan-2-ylpent-4-enoate

Product 1

HCID 127848185,5-Dichloro-3-methyl-2-(propan-2-yl)pent-4-enoic acidYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 23.41 g (0.0925 mol) of ethyl 5,5-dichloro-3-methyl-2-isopropyl-4-pentenoate, 11.10 g (0.278 mol) of sodium hydroxide, 40 ml of water, and 40 ml of ethanol was refluxed for 3 days under N2, the solvent was concentrated on the rotary evaporator, the residue taken up in 300 ml of water and extracted 2× with ether. The aqueous layer was acidified with conc. HCl, then extracted 3× with 150 ml of ether. The combined ether extracts were washed with water, dried (MgSO4), and stripped to give 17.09 g (82% yield) of the desired acid.

Workup

  1. concentrationthe solvent was concentrated on the rotary evaporator
  2. extractionextracted 2× with ether
  3. extractionextracted 3× with 150 ml of ether
  4. washThe combined ether extracts were washed with water
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-e835d842956f4a99842cf42bd7db5d79
Source dataset
uspto-grants-1982_07
Patent number
US04338326

Reaction notes

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