Potassium Hydroxide → 2-Methyl-2-(prop-2-yn-1-yl)propanedioic acid

HRID 4172

Reaction equation

HRID 4172 reaction equation
[CH3:1][C:2]([CH2:13][C:14]#[CH:15])([C:8]([O:10]CC)=[O:9])[C:3]([O:5]CC)=[O:4].[OH-].[K+]>O.C(O)C>[CH3:1][C:2]([CH2:13][C:14]#[CH:15])([C:3]([OH:5])=[O:4])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13924392Diethyl 2-methyl-2-propargyl-malonate

Product 1

HCID 139243932-Methyl-2-(prop-2-yn-1-yl)propanedioic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

187 g (0.88 mol) of diethyl 2-methyl-2-propargyl-malonate are added to a solution of 101 g (1.8 mol) of potassium hydroxide in a mixture of 560 ml of water/ethanol (1:1) and the mixture is refluxed with stirring for 2 hours. After the reaction has ended (monitored by TLC) the mixture is evaporated to dryness in vacuo and the residue is then taken up with in water. The aqueous solution is acidified with 50% sulphuric acid and extracted several times with methylene chloride. The combined extracts are dried, evaporated to dryness in vacuo and a colourless product is obtained, m.p. 135° C.

Workup

  1. temperaturethe mixture is refluxed
  2. customis evaporated to dryness in vacuo
  3. extractionextracted several times with methylene chloride
  4. customThe combined extracts are dried
  5. customevaporated to dryness in vacuo
  6. customa colourless product is obtained

Sources & evidence

ORD record
ord-f675b34133534fd2ad6348d7c4b67760
Source dataset
uspto-grants-1988_02
Patent number
US04724236

Linked notes

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