Hydrochloric Acid → HCID 66850639, compound

HRID 538950Notes

Reaction equation

HRID 538950 reaction equation
[CH:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[OH-].[Na+]>C(OCC)(=O)C>[CH:1]1([CH:7]([C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=2)[C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 14798Sodium HydroxideHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 66850639HCID 66850639, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

The synthesis of an amine hardener composition was carried out as follows: Cyclohexane carboxaldehyde (5 g, 44.6 mmol, 1 equiv) and aniline (12.5 g, 134.3 mmol, 3 equiv) were added to a 100 mL two-necked round bottom flask equipped with a condenser and thermocouple. The flask was placed under nitrogen and 0.25 mL concentrated HCl was added. After refluxing at 110° C. for 5 hours, the reaction was allowed to cool to 50° C. and 0.75 mL of 50 wt % aqueous NaOH was added. Ethyl acetate (EtOAc) was added and the solution was washed with water (3×30 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed in vacuo. The resulting mixture contained residual aniline. Purification of the material was performed via column chromatography (66:33 hexane:EtOAc) to yield a tacky yellow solid, 4,4′-(cyclohexylmethylene)dianiline [Structure (XI)], Rf=0.25.

Workup

  1. customequipped with a condenser
  2. temperatureto cool to 50° C.
  3. washthe solution was washed with water (3×30 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customPurification of the material

Sources & evidence

ORD record
ord-9082d001f661493ea90dc7d066a649a7
Source dataset
uspto-grants-2014_10
Patent number
US08865917B2

Reaction notes

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