Toluene → 1-Dodecyl-4-ethenylbenzene

HRID 1022276Notes

Reaction equation

HRID 1022276 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27]O)=[CH:22][CH:21]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:8]([C:20]1[CH:21]=[CH:22][C:23]([CH:26]=[CH2:27])=[CH:24][CH:25]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 21849437HCID 21849437, compound

Product 1

HCID 202659391-Dodecyl-4-ethenylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 2 l round-bottom flask which had been provided with a water separator and a reflux condenser was charged initially with 1.2 liters of toluene and then with (p-dodecylphenyl)methylcarbinol (50.082 g=0.173 mol) and p-toluenesulphonic acid monohydrate (0.679 g=3.6 mmol). The mixture was heated to reflux with constant stirring and kept at boiling until no further water separated out. Once the reaction mixture had been cooled to room temperature, the organic phase was extracted by shaking twice with 500 ml each time of water and once with 250 ml of saturated sodium chloride solution. After drying over magnesium sulphate, the solvent was drawn off on a rotary evaporator. A yellow oil was obtained. Subsequently, the two batches were combined. The crude product was purified by column chromatography on 400 g of silica gel 60 with hexane as the eluent, and a fraction size of 100 ml was selected.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customseparated out
  4. extractionthe organic phase was extracted
  5. stirringby shaking twice with 500 ml each time of water and once with 250 ml of saturated sodium chloride solution
  6. dry with materialAfter drying over magnesium sulphate
  7. customthe solvent was drawn off on a rotary evaporator
  8. customA yellow oil was obtained
  9. customThe crude product was purified by column chromatography on 400 g of silica gel 60 with hexane as the eluent

Sources & evidence

ORD record
ord-588080979e0f4042a32942ac70343942
Source dataset
uspto-grants-2014_05
Patent number
US08721929B2

Reaction notes

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