Hydrochloric Acid → 2-(prop-2-yn-1-yl)pent-4-ynoic acid

HRID 1585166Notes

Reaction equation

HRID 1585166 reaction equation
[CH2:1]([CH:4]([CH2:9][C:10]#[CH:11])[C:5]([O:7]C)=[O:6])[C:2]#[CH:3].[OH-].[Na+].Cl>O>[CH2:1]([CH:4]([CH2:9][C:10]#[CH:11])[C:5]([OH:7])=[O:6])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12014811HCID 12014811, compound

Product 1

HCID 136736532-(prop-2-yn-1-yl)pent-4-ynoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-(2-propynyl)-4-pentynoate (27.5 g) was saponified with sodium hydroxide (22 g) in refluxing water (250 ml). The solution was cooled and acidified with 12 N HCl to pH 3, and then extracted with t-butyl methyl ether. The organic layer was washed with brine and dried over sodium sulfate. Solvent removal afforded the title compound.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with t-butyl methyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent removal

Sources & evidence

ORD record
ord-6e03795827444be3b8c7a4df673e03fb
Source dataset
uspto-grants-1999_08
Patent number
US05936000

Reaction notes

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