Hydrochloric Acid → (3-Benzyloxy-4-nitrophenyl)acetonitrile

HRID 1358457Notes

Reaction equation

HRID 1358457 reaction equation
[OH-].[Na+].C([C:10]1[C:11]([N+:33]([O-:35])=[O:34])=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]3C=CC=CC=3)C=2[N+]([O-])=O)[CH:13]=[CH:14][CH:15]=1)C1C=CC=CC=1.C1(S[CH2:43][C:44]#[N:45])C=CC=CC=1.Cl>CS(C)=O>[CH2:17]([O:16][C:12]1[CH:13]=[C:14]([CH2:43][C:44]#[N:45])[CH:15]=[CH:10][C:11]=1[N+:33]([O-:35])=[O:34])[C:22]1[CH:21]=[CH:20][CH:19]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 78891(Phenylthio)acetonitrileHCID 57359178Benzyl-2-nitrophenyl Ether

Product 1

HCID 13629306(3-Benzyloxy-4-nitrophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of NaOH (68.44 g 1.71 mol, Aldrich, 20-40 mesh beads) in 171 mL of DMSO a solution of benzyl-2-nitrophenyl ether (39.23 g, 0.171 mol) and (phenylthio)acetonitrile (25.54 g, 0.171 mol, Lancaster) in 171 mL of DMSO was added dropwise for 10 min and stirred at r.t. for another 25 min. A mixture of 430 g of ice and 430 g of conc. HCl was added. The product precipitated and crystallized. The reaction mixture was cooled down in a refrigerator and filtered. The precipitate was dried on air (hood!) and recrystallized from EtOAc-hexanes. Yield 32.03 g (70%), mp 78-80° C.

Workup

  1. additionwas added dropwise for 10 min
  2. additionwas added
  3. customThe product precipitated
  4. customcrystallized
  5. temperatureThe reaction mixture was cooled down in a refrigerator
  6. filtrationfiltered
  7. customThe precipitate was dried on air (hood!)
  8. customrecrystallized from EtOAc-hexanes

Sources & evidence

ORD record
ord-07042c1f284e4e9f9227e21fb80c0ce4
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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