Sulfuric Acid → HCID 19783308, compound

HRID 257477Notes

Reaction equation

HRID 257477 reaction equation
[C:1]1([C:7](O)([CH2:9][CH:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH3:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:1]1(/[C:7](=[CH:9]/[CH:10]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)[CH3:11])/[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1(/[C:7](=[CH:9]\[CH:10]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)[CH3:11])/[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 19783299HCID 19783299, compound

Product 2

HCID 19783308HCID 19783308, compoundYield 17%HCID 67884051HCID 67884051, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To the said oily substance, that is , 8.83 g (36.6 mmol) of 2-phenyl-4-(4-pyridyl)-2-pentanol, 15 ml of 65% sulfuric acid was added and the mixture was heated for 2 hours at 100° C and after cooling, water was added. The mixture was alkalized with sodium carbonate and was extracted with ethyl acetate. Subsequently, layer a of ethyl acetate was dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure and purified by silica gel column chromatography to obtain 0.45 g of (E)-2-phenyl-4-(4-pyridyl)-2-pentene (yield: 17%) and 0.10 g of (Z)-2-phenyl-4-(4-pyridyl)-2-pentene (yield: 4%).

Workup

  1. temperatureafter cooling
  2. extractionwas extracted with ethyl acetate
  3. dry with materialSubsequently, layer a of ethyl acetate was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-5ad3d7a793774b45bf98375eccc02eb3
Source dataset
uspto-grants-1993_11
Patent number
US05262420

Reaction notes

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