p-Toluenesulfonic acid → 2-(2,2-Dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrile

HRID 1255558Notes

Reaction equation

HRID 1255558 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[OH:8].CO[C:14](OC)([CH3:16])[CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][C:14]1([CH3:16])[O:8][C:7]2[CH:6]=[CH:5][C:4]([CH2:9][C:10]#[N:11])=[CH:3][C:2]=2[O:1]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 109097272-(3,4-Dihydroxyphenyl)acetonitrile

Product 1

HCID 552677322-(2,2-Dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrileYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (3,4-dihydroxy-phenyl)-acetonitrile (0.2 g, 1.3 mmol) in toluene (4 mL) was added 2,2-dimethoxy-propane (0.28 g, 2.6 mmol) and TsOH (0.010 g, 0.065 mmol). The mixture was heated at reflux overnight. The reaction mixture was evaporated to remove the solvent and the residue was dissolved in ethyl acetate. The organic layer was washed with NaHCO3 solution, H2O, brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (Petroleum Ether/EtOAc 10:1) to give 2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrile (40 mg, 20%). 1H NMR (CDCl3, 400 MHz) δ 6.68-6.71 (m, 3H), 3.64 (s, 2H), 1.67 (s, 6H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customThe reaction mixture was evaporated
  4. customto remove the solvent
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe organic layer was washed with NaHCO3 solution, H2O, brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated under reduced pressure
  9. customto give a residue, which
  10. customwas purified by column chromatography on silica gel (Petroleum Ether/EtOAc 10:1)

Sources & evidence

ORD record
ord-b40b3fca6bfe4d82947bd67b3b0e5514
Source dataset
uspto-grants-2013_06
Patent number
US08461156B2

Reaction notes

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