Toluene → HCID 12292034, compound

HRID 1438922Notes

Reaction equation

HRID 1438922 reaction equation
[C:1]1(C)C=CC=CC=1.[C:8]([CH2:10][CH:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:18])#[N:9].CI>C1C=CC=CC=1>[C:8]([CH2:10][C:11]1([CH3:1])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:18])#[N:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6328Methyl iodideHCID 22757272HCID 22757272, compound

Product 1

HCID 12292034HCID 12292034, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
65 °C

Procedure

A solution of sodium tert.-amylate in toluene (340 ml, 0.297 mole) is added dropwise with stirring under nitrogen to a solution of 2-cyanomethylcycloheptanone (44.6 g, 0.297 mole, obtained as described above) and methyl iodide (42.6 g, 0.3 mole) in dry benzene (200 ml), and the mixture is stirred at 65° C for 4 hrs. and allowed to stand overnight at room temperature. The reaction mixture is washed with 1% aqueous hydrochloric acid, water, saturated sodium chloride solution, dried over magnesium sulfate, and the solvent is evaporated. Distillation of the residue under reduced pressure yields 2-cyanomethyl-2-methylcycloheptanone, bp. 152°-158° C/14 mm, nmr (CDCl3) δ1.27 (s, 3H).

Workup

  1. waitto stand overnight at room temperature
  2. washThe reaction mixture is washed with 1% aqueous hydrochloric acid, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is evaporated
  5. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-f04902f3409843288ba1067b4bddee05
Source dataset
uspto-grants-1977_11
Patent number
US04057559

Reaction notes

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