Formate → 3-Hydroxy-3-methylglutaric acid monoamide

HRID 1706591Notes

Reaction equation

HRID 1706591 reaction equation
[OH:1][C:2]([CH3:9])([CH2:6]C#N)[CH2:3][C:4]#[N:5].[OH:10]O.[CH:12]([O-:14])=[O:13]>[OH-].[Na+].O>[OH:1][C:2]([CH3:9])([CH2:6][C:12]([OH:14])=[O:13])[CH2:3][C:4]([NH2:5])=[O:10]

Participants

6

Reactant 3

HCID 283FormateHCID 784Hydrogen PeroxideHCID 127207073-Hydroxy-3-methylpentanedinitrile

Product 1

HCID 127207103-Hydroxy-3-methylglutaric acid monoamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 12.4 g (0.10 moles) of 3-hydroxy-3-methylglutaronitrile in 107 ml of 1.3 M sodium hydroxide is stirred at room temperature while 17.4 ml (0.20 moles) of 30% hydrogen peroxide is slowly added. After the addition of peroxide, the mixture is heated to boiling and boiling is maintained for 2 hours. Thereafter the mixture is cooled, diluted to 1 liter with water and passed through a 200 ml column of Dowex 2 resin in the formate form. The column is then washed with 1 liter of water. Thereafter the product is eluted with 1 liter of 0.1 N formic acid and the eluate evaporated to dryness to afford 3-hydroxy-3-methylglutaric acid monoamide.

Workup

  1. additionis slowly added
  2. temperaturethe mixture is heated
  3. temperatureboiling is maintained for 2 hours
  4. temperatureThereafter the mixture is cooled
  5. washThe column is then washed with 1 liter of water
  6. washThereafter the product is eluted with 1 liter of 0.1 N formic acid
  7. customthe eluate evaporated to dryness

Sources & evidence

ORD record
ord-a59c5a65fb1443c28d52f3c1dcc61690
Source dataset
uspto-grants-1980_06
Patent number
US04208204

Reaction notes

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