Water → HCID 57934612, compound

HRID 1433109Notes

Reaction equation

HRID 1433109 reaction equation
O.[CH2:2]([CH:14]1[CH2:19][CH2:18][CH:17](O)[CH2:16][CH2:15]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].S([O-])(O)(=O)=O.[K+]>C1(C)C(C)=CC=CC=1>[CH2:2]([CH:14]1[CH2:19][CH2:18][CH:17]=[CH:16][CH2:15]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 783684-Dodecylcyclohexan-1-olHCID 516920Potassium bisulfate

Product 1

HCID 57934612HCID 57934612, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A 1 L four-necked flask equipped with a mechanical stirrer, a thermometer, and a Dean-Stark water separator was charged with 4-n-dodecylcyclohexanol (0.372 mol), potassium hydrogen sulfate (0.187 mol), and xylene (100 g), and they were heated and refluxed for 16 hours. After completion of the reaction, the reaction mixture was filtered with a glass filter, the solvent was removed by vacuum distillation, and purification was carried out by silica gel column chromatography (silica gel 60 (70-230 mesh), manufactured by Merck Ltd., elution solvent: n-hexane). The reaction product thus obtained was subjected to vacuum distillation using a kugelrohr distillation apparatus at 130° C./30 Pa to give 68.32 g (73% yield) of 4-dodecyl-1-cyclohexene (Formula (12) below). The results of 1H-NMR of this product are shown below.

Workup

  1. customA 1 L four-necked flask equipped with a mechanical stirrer
  2. temperaturewere heated
  3. temperaturerefluxed for 16 hours
  4. customAfter completion of the reaction
  5. filtrationthe reaction mixture was filtered with a glass
  6. filtrationfilter
  7. customthe solvent was removed by vacuum distillation, and purification
  8. washwas carried out by silica gel column chromatography (silica gel 60 (70-230 mesh), manufactured by Merck Ltd., elution solvent: n-hexane)
  9. customThe reaction product thus obtained
  10. distillationwas subjected to vacuum distillation
  11. distillationa kugelrohr distillation apparatus at 130° C./30 Pa

Sources & evidence

ORD record
ord-51e47197eb3642acb0778deae9339da9
Source dataset
uspto-grants-2009_11
Patent number
US07612123B2

Reaction notes

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