Toluene → HCID 178444394, compound

HRID 1936324Notes

Reaction equation

HRID 1936324 reaction equation
OC([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C@H:16]3CC[C@H](CCCCC)C[CH2:17]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)C.S([O-])(O)(=O)=O.[K+].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CCOCC>[CH2:39]([C@H:33]1[CH2:38][CH2:37][C@H:36]([CH:17]=[CH:16][C:13]2[CH:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=3)=[CH:15][CH:14]=2)[CH2:35][CH2:34]1)[CH2:9][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 516920Potassium bisulfateHCID 178444263HCID 178444263, compound

Product 1

HCID 178444394HCID 178444394, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

First, 9.39 g of 4-(1-hydroxyethyl)-4′-(trans-4-pentylcyclohexyl)biphenyl, 0.52 g of potassium hydrogensulfate, and 50 ml of toluene were put in a 300 ml flask provided with a water content quantitative tube, and subjected to azeotropic dehydration under reflux for four hours. After the reaction, ether was added to the reaction solution, which was then washed with a saturated brine, and dried with sodium sulfate. The solvent was then distilled off. The residue was recrystallized from hexane to obtain 1.88 g (Y: 21.1%) of 4-(trans-4-pentylcyclohexyl)vinylbiphenyl. The purity of the resultant compound was 100.0% as measured by GC, 99.9% as measured by HPLC, and 1 spot as measured by TLC. The phase transfer temperature of the resultant compound was as follows.

Workup

  1. customprovided with a water content quantitative tube
  2. temperatureunder reflux for four hours
  3. additionwas added to the reaction solution, which
  4. washwas then washed with a saturated brine
  5. dry with materialdried with sodium sulfate
  6. distillationThe solvent was then distilled off
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-ef0879f52ae94ea8b4fa3c32733240d0
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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