Ammonia → 3,3-dicyclopropylpropanoic Acid

HRID 1769942Notes

Reaction equation

HRID 1769942 reaction equation
[OH-:1].[K+].[CH:3]1([CH:6]([CH:10]2[CH2:12][CH2:11]2)[CH2:7][C:8]#N)[CH2:5][CH2:4]1.N.Cl.[OH2:15]>C(O)COCCO>[CH:3]1([CH:6]([CH:10]2[CH2:12][CH2:11]2)[CH2:7][C:8]([OH:15])=[O:1])[CH2:5][CH2:4]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 107730223,3-Dicyclopropylpropionitrile

Product 1

HCID 108445973,3-dicyclopropylpropanoic AcidYield 83%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

45 g of potassium hydroxide are dissolved in 65 ml of water. 100 ml of diethylene glycol are added to the above solution followed by 30 g of the product obtained in stage A. The mixture is refluxed until the evolution of ammonia ceases. After cooling, 700 ml of water are added and the mixture is acidified with 12N hydrochloric acid. After extraction with ether, the ethereal phases are pooled, washed with water until neutral, dried and evaporated. The expected product is obtained after distillation.

Workup

  1. temperatureAfter cooling
  2. extractionAfter extraction with ether
  3. washwashed with water until neutral,
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-f9a0aade3d0e4826a28768ab8236e300
Source dataset
uspto-grants-1995_01
Patent number
US05384322

Reaction notes

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