Water → 2-(Methyloxy)-4-(2-oxoethyl)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:11][CH:10]2C(OCC)=O)=[CH:5][C:4]=1[O:17][CH3:18])#[N:2].CC[O-].[Na+].O>C(O)C>[CH3:18][O:17][C:4]1[CH:5]=[C:6]([CH2:9][CH:10]=[O:11])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of ethyl 3-(4-cyano-3-methoxyphenyl)oxirane-2-carboxylate (400 mg, 1.6 mmol) in 5 mL of dry ethanol was cooled to 0° C. Freshly prepared EtONa (2.1 mmol) in 4 mL of ethanol was added and stirred at 0° C. 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 10 mL of water and added 10 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 crude 2-methoxy-4-(2-oxoethyl)benzonitrile. MS m/z: 176 (M+1)+.
Workup
- stirringstirred at 0° C. for 2 hours
- filtrationthe sodium salt of the epoxy compound was filtered
- dissolutionThe sodium salt of the epoxy compound was then dissolved in 10 mL of water
- additionadded 10 mL of 1 N of HCl and 20 mL of toluene
- temperatureThe mixture was heated
- temperatureto reflux for 2 hours
- customThe organic phase was separated
- washwashed by saturated sodium chloride
- dry with materialdried over Na2SO4
- distillationdistilled off solvent
Sources & evidence
- ORD record
- ord-dde40bc9d9dd435aa0f7db05a047adc8
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073882B2
Reaction notes
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