Sulfuric Acid → HCID 57934610, compound

HRID 1433110Notes

Reaction equation

HRID 1433110 reaction equation
[C:1]([CH:9]1[CH2:14][CH2:13][CH:12](O)[CH2:11][CH2:10]1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O>[C:1]([CH:9]1[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]1)([CH2:4][C:5]([CH3:7])([CH3:8])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24436Sodium SulfateHCID 546355Cyclohexanol, 4-(1,1,3,3-tetramethylbutyl)-

Product 1

HCID 57934610HCID 57934610, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L four-necked flask equipped with a mechanical stirrer, a thermometer, and a Dean-Stark water separator was charged with 4-t-octylcyclohexanol (0.471 mol), sulfuric acid (0.047 mol), sodium sulfate (0.047 mol), distilled water (35 g), and xylene (100 g), and they were heated and refluxed for 3 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 120° C./666 Pa to give 85.64 g (94% yield) of 4-t-octyl-1-cyclohexene (Formula (14) 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. distillationdistilled water (35 g), and xylene (100 g), and they
  3. temperaturewere heated
  4. temperaturerefluxed for 3 hours
  5. customAfter completion of the reaction
  6. filtrationthe reaction mixture was filtered with a glass
  7. filtrationfilter
  8. customthe solvent was removed by vacuum distillation, and purification
  9. washwas carried out by silica gel column chromatography (silica gel 60 (70-230 mesh), manufactured by Merck Ltd., elution solvent: n-hexane)
  10. customThe reaction product thus obtained
  11. distillationwas subjected to vacuum distillation
  12. distillationa kugelrohr distillation apparatus at 120° C./666 Pa

Sources & evidence

ORD record
ord-ae9dcc263bfc4a7bb1ddfc788b03c71a
Source dataset
uspto-grants-2009_11
Patent number
US07612123B2

Reaction notes

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