p-Toluenesulfonic acid → HCID 21825359, compound

HRID 267226Notes

Reaction equation

HRID 267226 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:31](O)[CH2:32][CH2:33][OH:34].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:8]2([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[O:34][CH2:33][CH2:32][CH2:31][O:9]2)[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 516892Sodium BicarbonateHCID 126232692-(3,4-Dimethoxybenzoyl)-6-methylpyridine

Product 1

HCID 21825359HCID 21825359, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

About 77.1 g. of (3,4-dimethoxyphenyl) (6-methyl-2-pyridyl) ketone, 74.1 g. of p-toluenesulfonic acid and 22.8 ml of 1,3-propanediol in 600 ml of toluene were heated under reflux with stirring for 17 hours. The water evolved during the reaction was neutralized with 500 ml of saturated sodium bicarbonate. Two phases formed and the phases were separated. The organic layer was washed with saturated sodium bicarbonate solution and dried over magnesium sulfate. Removal of the desiccant and solvent gave a solid residue which, on recrystallization from a mixture of acetone and petroleum ether (b.p. 60°-80°C.), yielded 2-(3,4-dimethoxyphenyl)-2-(6-methyl-2-pyridyl)-1,3-dioxane, m.p. 124°-126°C.

Workup

  1. temperatureunder reflux
  2. customTwo phases formed
  3. customthe phases were separated
  4. washThe organic layer was washed with saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the desiccant and solvent
  7. customgave a solid residue which
  8. customon recrystallization
  9. additionfrom a mixture of acetone and petroleum ether (b.p. 60°-80°C.)

Sources & evidence

ORD record
ord-42a08db92df4430580a07c155ef81c4c
Source dataset
uspto-grants-1976_03
Patent number
US03941796

Reaction notes

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