Ethylenediamine → P-Cymene

HRID 1844760Notes

Reaction equation

HRID 1844760 reaction equation
C(N)CN.[Na].[H][H].[CH3:8][C:9]1[CH2:14][CH2:13][CH:12]([C:15]([CH3:17])=[CH2:16])[CH2:11][CH:10]=1>O>[C:12]1([CH:15]([CH3:17])[CH3:16])[CH:13]=[CH:14][C:9]([CH3:8])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 223111-Methyl-4-Prop-1-En-2-YlcyclohexeneHCID 5360545Sodium2×HCID 178418361HCID 178418361, compound

Product 1

HCID 7463P-CymeneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To mixture of ethylenediamine (525 mmol, 31.6 g, 35.2 ml), anhydrous FeCl3 (0,964 mmol, 0.16 g) and sodium (145 mmol, 3.34 g) was heated to about 50° C. under N2. After sodium dissolution had started, as evidenced by hydrogen evolution and formation of a dark solution, α-limonene (742 mmol, 101 g, 120 ml), certified as derived from biomass (obtained from Sigma-Aldrich (St. Louis, Mo.), was added dropwise into the mixture and the mixture heated to 100° C. The mixture was heated at 100° C. for 8 h. The mixture was then cooled down and diluted with water (300 ml) and extracted two times with dichloro methane (DCM) (300 ml). The organic layers were dried over magnesium sulfate and concentrated using a rotary evaporator obtaining the crude para-cymene product. Yield: 99% (purity 99%)

Workup

  1. additionwas added dropwise into the mixture
  2. temperaturethe mixture heated to 100° C
  3. temperatureThe mixture was heated at 100° C. for 8 h
  4. temperatureThe mixture was then cooled down
  5. extractionextracted two times with dichloro methane (DCM) (300 ml)
  6. dry with materialThe organic layers were dried over magnesium sulfate
  7. concentrationconcentrated
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-7d5be1c62beb46d09dbe6549f7953cc0
Source dataset
uspto-grants-2015_02
Patent number
US08946472B2

Reaction notes

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