Sulfuric Acid → HCID 67884339, compound

HRID 257475Notes

Reaction equation

HRID 257475 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](O)([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:8])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:11]1([CH2:10]/[CH:9]=[C:7](/[C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)\[CH3:8])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1.[C:11]1([CH2:10][CH2:9][C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[CH2:8])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 19783310HCID 19783310, compound

Product 2

HCID 19783363HCID 19783363, compoundYield 11.5%HCID 67884339HCID 67884339, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To the said alcoholic substance, that is 1.42 g of 2-(4-pyridyl)-4-phenyl-2-butanol, 4 ml of 65% sulfuric acid was added and the mixture was stirred for two hours at 100° C. After cooling, water was added and the mixture was alkalized with sodium carbonate to extract with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure to obtain viscous oily substance. The said oily substance was purified by silica gel column chromatography to obtain 0.44 g of (E)-1-phenyl-3-(4-pyridyl)-2-butene (yield: 33.7%) and 0.15 g of 4-phenyl-2-(4-pyridyl)-1-butene (yield: 11.5%).

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionto extract with ethyl acetate
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customto obtain viscous oily substance
  7. customThe said oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-25d3738c78eb4924a4fa67351b6c44af
Source dataset
uspto-grants-1993_11
Patent number
US05262420

Reaction notes

Loading…