Ethanol → 3-Methyl-2-(propan-2-yl)pent-4-ynoic acid

HRID 905251Notes

Reaction equation

HRID 905251 reaction equation
[CH:1]([CH:4]([CH:10]([CH3:13])[C:11]#[CH:12])[C:5]([O:7]CC)=[O:6])([CH3:3])[CH3:2].[OH-].[Na+].C(O)C>O>[CH:1]([CH:4]([CH:10]([CH3:13])[C:11]#[CH:12])[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13227602Ethyl 3-methyl-2-(propan-2-yl)pent-4-ynoate

Product 1

HCID 132694973-Methyl-2-(propan-2-yl)pent-4-ynoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 250 milliliter flask was equipped with a magnetic stirrer, reflux condenser and nitrogen inlet. Into the flask was added 8.44 grams (0.05 mol) of ethyl 2-isopropyl-3-methyl-4-pentynoate prepared in Part B, 5.56 grams (0.14 mol) of sodium hydroxide, 20 milliliters of ethanol and 20 milliliters of water. Following three days of continuous refluxing and stirring under nitrogen, the reaction mixture was cooled to room temperature, diluted with three times its volume of water and extracted twice with ether. Ice was added to the aqueous phase and it was acidified with 3 N HCl, then extracted three times with ether. The ether was washed twice with water, dried (MgSO4) and removed under vacuum to give 5.87 grams (0.04 mol) of 2-isopropyl-3-methyl-4-pentynoic acid having the appearance of a light yellow oil.

Workup

  1. customA 250 milliliter flask was equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. temperatureof continuous refluxing
  4. extractionextracted twice with ether
  5. additionIce was added to the aqueous phase and it
  6. extractionextracted three times with ether
  7. washThe ether was washed twice with water
  8. dry with materialdried (MgSO4)
  9. customremoved under vacuum

Sources & evidence

ORD record
ord-f4340d5814014205afa89c9baaf8e440
Source dataset
uspto-grants-1983_12
Patent number
US04423064

Reaction notes

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