Water → 3-Methyl-4-(2-oxoethyl)benzonitrile

HRID 1519578Notes

Reaction equation

HRID 1519578 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:11][CH:10]2C(OCC)=O)=[C:5]([CH3:17])[CH:4]=1)#[N:2].CC[O-].[Na+].O>C(O)C>[CH3:17][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[CH2:9][CH:10]=[O:11])[C:1]#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 86694473Ethyl 3-(4-cyano-2-methylphenyl)oxirane-2-carboxylate

Product 1

HCID 772306903-Methyl-4-(2-oxoethyl)benzonitrileYield 20.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of ethyl 3-(4-cyano-2-methylphenyl)oxirane-2-carboxylate (927 mg, 4.0 mmol) in 10 mL of dry ethanol was cooled to 0° C. Freshly prepared EtONa (12.4 mmol) in 8 mL of ethanol was added and stirred at 0 for 10 min. Then dropwise addition of 0.1 g of water, stirred at 0° C. for 2 hours, and the sodium salt of the epoxy compound was filtered. The sodium salt of the epoxy compound was then dissolved in 5 mL of water and added 5 mL of 1 N of HCl and 20 mL of toluene. The mixture was heated to reflux for 2 hours. The organic phase was separated, washed by saturated sodium chloride, dried over Na2SO4 and distilled off solvent to afford 130 mg of crude 3-methyl-4-(2-oxoethyl)benzonitrile. MS m/z: 160 (M+1)+.

Workup

  1. stirringstirred at 0° C. for 2 hours
  2. filtrationthe sodium salt of the epoxy compound was filtered
  3. dissolutionThe sodium salt of the epoxy compound was then dissolved in 5 mL of water
  4. additionadded 5 mL of 1 N of HCl and 20 mL of toluene
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 2 hours
  7. customThe organic phase was separated
  8. washwashed by saturated sodium chloride
  9. dry with materialdried over Na2SO4
  10. distillationdistilled off solvent

Sources & evidence

ORD record
ord-0c893269c8b94f85b1294a6d0a9b5ea0
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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