Water → 1-(3-[1,3]dioxolan-2-yl-4-methoxy-phenyl)-1H-tetrazole

HRID 1456309Notes

Reaction equation

HRID 1456309 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[CH:7][C:4]=1[CH:5]=[O:6].[C:16]1([CH3:26])C=CC(S(O)(=O)=O)=CC=1.[OH2:27]>C1(C)C=CC=CC=1.C(O)CO>[O:6]1[CH2:26][CH2:16][O:27][CH:5]1[C:4]1[CH:7]=[C:8]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)[CH:9]=[CH:10][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 105361692-Methoxy-5-tetrazol-1-yl-benzaldehyde

Product 1

HCID 110430831-(3-[1,3]dioxolan-2-yl-4-methoxy-phenyl)-1H-tetrazole

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 2-methoxy-5-tetrazol-1-yl-benzaldehyde (8 g) in toluene (400 ml), ethylene glycol (8 ml) and para-toluene sulphonic acid (50 mg) were added. The mixture was heated to reflux under Dean-Stark conditions and under a nitrogen atmosphere for 12 h whereupon evolution of water had ceased. The mixture was allowed to cool and the liquor decanted and extracted with 8% aqueous sodium bicarbonate solution (100 ml). The precipitated solid was dissolved in dichloromethane (200 ml) and then extracted with the aqueous layer. The aqueous layer was then extracted with dichloromethane (100 ml). The organic layers were then combined, dried (Na2SO4) and evaporated in vacuo to yield the title compound as a yellow solid (9.12 g).

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto cool
  4. customthe liquor decanted
  5. extractionextracted with 8% aqueous sodium bicarbonate solution (100 ml)
  6. dissolutionThe precipitated solid was dissolved in dichloromethane (200 ml)
  7. extractionextracted with the aqueous layer
  8. extractionThe aqueous layer was then extracted with dichloromethane (100 ml)
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-f8136573919c47579c1649177ba1bae1
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

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