Sulfuric Acid → HCID 12426932, compound

HRID 1193645Notes

Reaction equation

HRID 1193645 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[N:14]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1>>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([CH:20]([C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=2)[C:17]2[CH:16]=[CH:15][N:14]=[CH:19][CH:18]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7519AnisoleHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 12426932HCID 12426932, compound

Conditions

Temperature
70 °C

Procedure

Anisole, 108.13 g (1.0 mole) was cooled in an ice bath. Concentrated sulfuric acid, 115.3 ml (2.0 mole) was added while stirring the mixture in an ice bath. The temperature rose to 55° C. The reaction was then cooled in the ice bath. To this solution was added 4-pyridine carboxaldehyde, 53.5 g (0.5 mole). The temperature rose to 95° C. and further cooling and stirring brought the temperature down to 20° C. The reaction mixture was heated to 70° C. for 31/2 hr. The red gel was made alkaline with 50% sodium hydroxide-ice mix. The alkaline phase was extracted with toluene and the toluene extracted with a saturated sodium chloride solution. The product crystallized from the toluene solution while standing at room temperature. The white solid can be recrystallized from hot hexane-isopropyl alcohol.

Workup

  1. customrose to 55° C
  2. customrose to 95° C.
  3. temperaturefurther cooling
  4. stirringstirring
  5. customdown to 20° C
  6. additionmix
  7. extractionThe alkaline phase was extracted with toluene
  8. extractionthe toluene extracted with a saturated sodium chloride solution
  9. customThe product crystallized from the toluene solution
  10. customwhile standing at room temperature
  11. customThe white solid can be recrystallized from hot hexane-isopropyl alcohol

Sources & evidence

ORD record
ord-81ef6e9ef4bb499ca561f33d9d6b3ab5
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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