Ammonium Hydroxide → 3-Hydroxy-3-methylglutaric acid monoamide, ammonium salt

HRID 1706593Notes

Reaction equation

HRID 1706593 reaction equation
[OH:1][C:2]1([CH3:10])[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.[OH-].[NH4+:12]>>[NH4+:12].[OH:1][C:2]([CH3:10])([CH2:8][C:7]([O-:6])=[O:9])[CH2:3][C:4]([NH2:12])=[O:5]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 52394304-Hydroxy-4-methyloxane-2,6-dione

Product 1

HCID 1317117913-Hydroxy-3-methylglutaric acid monoamide, ammonium salt

Procedure

1.7 g. (0.011 moles) of 3-hydroxy-3-methylglutaric acid anhydride (prepared according to the method of Hilz, et al, Biochem Zeit, 329, 476-489 (1958)) in 30 ml of 15 N ammonium hydroxide is allowed to stand at 25° C. for 10 minutes. The solution is then evaporated to dryness under vacuum and the resulting residue dissolved in 10 ml of warm methanol. Ethyl acetate (10 ml) is then slowly added to the methanol solution. Upon cooling, 1.5 g. of 3-hydroxy-3-methylglutaric acid monoamide, ammonium salt is obtained as a white crystalline solid.

Workup

  1. customThe solution is then evaporated to dryness under vacuum
  2. dissolutionthe resulting residue dissolved in 10 ml of warm methanol
  3. additionEthyl acetate (10 ml) is then slowly added to the methanol solution
  4. temperatureUpon cooling

Sources & evidence

ORD record
ord-df7f9b89d17546a5b91da40096676264
Source dataset
uspto-grants-1980_06
Patent number
US04208204

Reaction notes

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