Toluene → HCID 12292034, compound

HRID 65621Notes

Reaction equation

HRID 65621 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:9][C:10]#[N:11].CI.[CH3:14]CC([O-])(C)C.[Na+].C1(C)C=CC=CC=1>C1C=CC=CC=1>[CH3:14][C:3]1([CH2:9][C:10]#[N:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 2733478Sodium 2-methylbutan-2-olateHCID 22757272HCID 22757272, compound

Product 1

HCID 12292034HCID 12292034, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 2-oxocycloheptaneacetonitrile (44.6 g, 0.297 mole), and methyl iodide (42.6 g, 0.3 mole) in dry benzene (200 ml) under nitrogen, is added dropwise a solution of sodium tert-amylate in toluene (340 ml, 0.297 mole). The reaction is exothermic and a bright yellow colour appears. The mixture is stirred at 65° C. for 4 hr., then allowed to stand overnight at room temperature. The mixture is washed with 1% aqueous HCl, cold water, then brine, dried (MgSO4) and concentrated to give an oily residue. Distillation under reduced pressure gives 1-methyl-2-oxocycloheptaneacetonitrile (13, R1 = CH3, R2 = H and m = 4), bp 152°-158° C./14 mm.

Workup

  1. waitto stand overnight at room temperature
  2. washThe mixture is washed with 1% aqueous HCl, cold water
  3. dry with materialbrine, dried (MgSO4)
  4. concentrationconcentrated
  5. customto give an oily residue
  6. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-4d24a214880d4b8382ee15a4a3158af0
Source dataset
uspto-grants-1978_12
Patent number
US04128560

Reaction notes

Loading…