Ethanol → 4-Chloro-2-(propan-2-yl)pent-4-enoic acid

HRID 2412463Notes

Reaction equation

HRID 2412463 reaction equation
[Cl:1][C:2](=[CH2:13])[CH2:3][CH:4]([CH:10]([CH3:12])[CH3:11])[C:5]([O:7]CC)=[O:6].C(O)C.[OH-].[Na+]>O>[Cl:1][C:2](=[CH2:13])[CH2:3][CH:4]([CH:10]([CH3:11])[CH3:12])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13370940HCID 13370940, compound

Product 1

HCID 133709414-Chloro-2-(propan-2-yl)pent-4-enoic acidYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The ethyl 4-chloro-2-isopropyl-4-pentenoate (8.0 g, 0.039 mol) was refluxed for 20 hrs. in 15 ml of water and 15 ml of ethanol containing 4.8 g (0.12 mol) of sodium hydroxide. Most of the ethanol was removed on the rotary evaporator and the residue taken up in 100 ml of water. The aqueous solution was extracted with two 50 ml portions of ether, then acidified with conc. HCl. The acidified mixture was extracted twice with 100 ml of ether. The ether was washed with water, dried (MgSO4), and removed to leave 4.83 g (70% yield) of a light yellow oil.

Workup

  1. customMost of the ethanol was removed on the rotary evaporator
  2. extractionThe aqueous solution was extracted with two 50 ml portions of ether
  3. extractionThe acidified mixture was extracted twice with 100 ml of ether
  4. washThe ether was washed with water
  5. dry with materialdried (MgSO4)
  6. customremoved

Sources & evidence

ORD record
ord-f9a2d4deca2843888358603d67f89cf2
Source dataset
uspto-grants-1985_01
Patent number
US04492799

Reaction notes

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