Sodium Hydroxide → 2-(4-(4-Methylpyridin-2-yl)-2-nitrophenyl)-1,3-dioxolane

HRID 1060016Notes

Reaction equation

HRID 1060016 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=2)[CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].[OH2:25].[C:26]1([CH3:36])C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)CO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]3[O:25][CH2:26][CH2:36][O:13]3)=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 521998p-Toluenesulfonic acid monohydrateHCID 186675944-(4-Methylpyridin-2-yl)-2-nitrobenzaldehyde

Product 1

HCID 186674852-(4-(4-Methylpyridin-2-yl)-2-nitrophenyl)-1,3-dioxolaneYield 75.2%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 4-(4-methylpyridin-2-yl)-2-nitrobenzaldehyde (242 mg), ethyleneglycol (1.2 ml) and magnesium sulfate (1.0 g) in toluene (5 ml) was added p-toluenesulfonic acid monohydrate (209 mg), and the resultant suspension was refluxed for 5 hours. After cooling, the mixture was poured into 0.1N aqueous sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, 25% ethyl acetate in n-hexane) to give 2-(4-(4-methylpyridin-2-yl)-2-nitrophenyl)-1,3-dioxolane (215 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 25 g, 25% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-bc74aeee989445379a738542868f71b8
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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