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

HRID 1463764Notes

Reaction equation

HRID 1463764 reaction equation
C[O:2][C:3](=[O:13])[C:4]([CH3:12])([CH2:9][C:10]#[CH:11])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO.O>[CH3:12][C:4]([CH2:9][C:10]#[CH:11])([C:3]([OH:13])=[O:2])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 187304062-Methyl-2-(2-propinyl)-malonic acid dimethyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

23.7 g [53] (127 mmol) were dissolved in 200 ml methanol and a solution of 28.3 g (708 mmol) of NaOH in 50 ml water was slowly added dropwise. The mixture was heated to 50° C. in a water bath for two hours, the solvent was removed in a rotary evaporator and the residue was dissolved in water. The mixture was acidified with semi-concentrated hydrochloric acid and the free carboxcylic acid was exacted with chloroform, washed and dried.

Workup

  1. customthe solvent was removed in a rotary evaporator
  2. dissolutionthe residue was dissolved in water
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-c9e10abe9ccc4102b9ca29dd643bc55f
Source dataset
uspto-grants-1994_04
Patent number
US05302370

Reaction notes

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