Water → 2-(3,3,5,5-Tetramethylcyclohexyl)phenylamine

HRID 604842Notes

Reaction equation

HRID 604842 reaction equation
C(O)(=O)C(O)=O.[CH3:7][C:8]1([CH3:23])[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])[CH2:9]1.[OH-].[K+].O>COC(C)(C)C>[CH3:7][C:8]1([CH3:23])[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])[CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67038669HCID 67038669, compound

Product 1

HCID 119922852-(3,3,5,5-Tetramethylcyclohexyl)phenylamineYield 97.5%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

2-(3,3,5,5-Tetramethylcyclohexyl)phenylamine oxalate (4.52 g, 14.1 mmol) was suspended in t-butyl methyl ether (45 mL), and a 1N aqueous solution of potassium hydroxide (16.9 mL) was added, followed by stirring at room temperature for 50 minutes. To the reaction mixture were added t-butyl methyl ether (15 mL) and water (25 mL), and the reaction mixture was stirred at room temperature, and the organic layer was separated. The organic layer was washed with water (23 mL) four times, the solvent was removed under reduced pressure to give 3.18 g of 2-(3,3,5,5-tetramethylcyclohexyl)phenylamine as a red oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature
  2. customthe organic layer was separated
  3. washThe organic layer was washed with water (23 mL) four times
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-728e361c83464b54afdabd8827680cd6
Source dataset
uspto-grants-2011_03
Patent number
US07910734B2

Reaction notes

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