Potassium Hydroxide → 1-Mesityl-2-methylpropan-2-amine

HRID 966103Notes

Reaction equation

HRID 966103 reaction equation
[CH3:1][C:2]([NH:14]C=O)([CH3:13])[CH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=1[CH3:12].[OH-].[K+]>C(O)CO>[CH3:13][C:2]([NH2:14])([CH3:1])[CH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=1[CH3:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22314552N-[1,1-dimethyl-2-(2,4,6-trimethylphenyl)ethyl]formamide

Product 1

HCID 625487981-Mesityl-2-methylpropan-2-amine

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

61 g of N-[1,1-dimethyl-2-(2,4,6-trimethylphenyl)ethyl]formamide is refluxed with 35 g of potassium hydroxide in 155 mL ethylene glycol for 9 hours with stirring and, after the reaction has ended, the mixture is poured onto 1 kg of ice. The aqueous phase is extracted three times with diethyl ether and the solvent is distilled off under reduced pressure. The residue is fractionally distilled. Yield: 48 g (89%); bp15: 135° C.-140° C.

Workup

  1. extractionThe aqueous phase is extracted three times with diethyl ether
  2. distillationthe solvent is distilled off under reduced pressure
  3. distillationThe residue is fractionally distilled
  4. custom135° C.-140° C.

Sources & evidence

ORD record
ord-edb3ba6cf1d241c18bc4e0a7518cccb2
Source dataset
uspto-grants-2005_10
Patent number
US06951888B2

Reaction notes

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