Potassium Hydroxide → 2-Methyl-2-(pent-4-yn-1-yl)propanedioicacid

HRID 1197363Notes

Reaction equation

HRID 1197363 reaction equation
[CH3:1][C:2]([CH2:13][CH2:14][CH2:15][C:16]#[CH:17])([C:8]([O:10]CC)=[O:9])[C:3]([O:5]CC)=[O:4].[OH-].[K+]>C(O)C>[CH3:1][C:2]([CH2:13][CH2:14][CH2:15][C:16]#[CH:17])([C:3]([OH:5])=[O:4])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19373418Diethyl 2-methyl-2-(pent-4-ynyl)malonate

Product 1

HCID 193733782-Methyl-2-(pent-4-yn-1-yl)propanedioicacid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 2-methyl-2-(pent-4-ynyl)malonate (11 g) and potassium hydroxide (15 g) in 95% ethanol (150 ml) was heated to reflux for 4 hours and then stood at room temperature for 15 hours. The bulk of the solvent was removed in vacuo and the residue was taken up in water. The resulting aqueous phase was washed with dichloromethane before acidification to pH 1 with concentrated hydrochloric acid and further extraction with fresh dichloromethane. These organic extracts were washed with brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. 2-Methyl-2-(pent-4-ynyl)malonic acid was obtained as a pale yellow solid (6.7 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customThe bulk of the solvent was removed in vacuo
  4. washThe resulting aqueous phase was washed with dichloromethane before acidification to pH 1 with concentrated hydrochloric acid and further extraction with fresh dichloromethane
  5. washThese organic extracts were washed with brine
  6. dry with materialbefore drying over anhydrous magnesium sulphate and evaporation in vacuo

Sources & evidence

ORD record
ord-290fb43b7c214a4db56f0efde574f2fa
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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