Sodium Hydroxide → HCID 18631024, compound

HRID 1060018Notes

Reaction equation

HRID 1060018 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=2)[CH:4]=1.S([O-])([O-])(=O)=O.[Mg+2].[OH2:26].[C:27]1([CH3:37])C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]3[O:26][CH2:27][CH2:37][O:14]3)=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=2)[CH:4]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 521998p-Toluenesulfonic acid monohydrateHCID 186675454-(4-Methoxypyridin-2-yl)-2-nitrobenzaldehyde

Product 1

HCID 18631024HCID 18631024, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 4-(4-methoxypyridin-2-yl)-2-nitrobenzaldehyde (413 mg), ethyleneglycol (0.266 ml) and magnesium sulfate (1.0 g) in toluene (10 ml) was added p-toluenesulfonic acid monohydrate (334 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 potassium carbonate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether. The solid was collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give 2-(4-(4-methoxypyridin-2-yl)-2-nitrophenyl)-1,3-dioxolane (412 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over potassium carbonate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with diisopropyl ether
  7. filtrationThe solid was collected by filtration
  8. washwashed with diisopropyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-cec6957867a8411081f101e28edb2960
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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