Pyridine → HCID 23191325, compound

HRID 743921Notes

Reaction equation

HRID 743921 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]([CH3:14])=[CH2:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>C(OCC)C.O1CCOCC1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:12]([O:11][CH3:10])([CH3:14])[CH3:13])=[CH:3][CH:4]=1)=[CH2:7]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 83002-MethoxypropeneHCID 624534-Vinylphenol

Product 1

HCID 23191325HCID 23191325, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

72.1 g (600 mmol) of 4-hydroxystyrene are dissolved in a mixture of 300 ml of diethyl ether and 150 ml of dioxane under a nitrogen atmosphere in a 1500 ml sulfonation flask. 216.3 g (3000 mmol) of 2-methoxypropene are added, and the mixture is cooled to 10° C. 1,48 g (7.8 mmol) of p-toluenesulfonic acid in 28.5 g (360 mmol) of pyridine are then added dropwise in the course of 20 minutes, and the mixture is stirred at room temperature for 20 hours. The reaction mixture is washed three times with 300 ml of 0.2N NaOH and three times with 300 ml of demineralized water. The organic phase is dried using magnesium sulfate, filtered through 1 cm of Ambefiyst A27 and evaporated in a rotary evaporator. Further drying of the resultant residue under a high vacuum leaves 99.2 g (82% of theory) of the desired product in the form of a yellow oil.

Workup

  1. washThe reaction mixture is washed three times with 300 ml of 0.2N NaOH and three times with 300 ml of demineralized water
  2. customThe organic phase is dried
  3. filtrationfiltered through 1 cm of Ambefiyst
  4. customand evaporated in a rotary evaporator
  5. dry with materialFurther drying of the resultant residue under a high vacuum

Sources & evidence

ORD record
ord-e133297cd0d34babbc956fcb6d1fd429
Source dataset
uspto-grants-1996_09
Patent number
US05558978

Reaction notes

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