Water → Ethyl 3-(4-cyano-2-methylphenyl)oxirane-2-carboxylate

HRID 1519577Notes

Reaction equation

HRID 1519577 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[CH3:11])=[O:2].[CH2:12]([O:14][C:15](=[O:18])[CH2:16]Cl)[CH3:13].CC[O-].[Na+].O>C1C=CC=CC=1.C(O)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[O:2][CH:16]2[C:15]([O:14][CH2:12][CH3:13])=[O:18])=[C:4]([CH3:11])[CH:5]=1)#[N:8]

Participants

7

Reactant 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 2723922Sodium ethoxideHCID 109096954-Formyl-3-methylbenzonitrile

Product 1

HCID 86694473Ethyl 3-(4-cyano-2-methylphenyl)oxirane-2-carboxylateYield 73.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A mixture of 4-formyl-3-methylbenzonitrile (1.5 g, 10.3 mmol) and chloroacetic acid ethyl ester (1.2 g, 10 mmol) were dissolved in 60 mL of dry benzene. Freshly prepared EtONa (12.4 mmol) in 8 mL of ethanol was added, and the mixture were stirred at room temperature for 2 hours. The mixture was added water, then extracted with EA, dried over Na2SO4 and distilled off solvent to afford 1.7 g of crude ethyl 3-(4-cyano-2-methylphenyl)oxirane-2-carboxylate. MS m/z: 232 (M+1)+.

Workup

  1. extractionextracted with EA
  2. dry with materialdried over Na2SO4
  3. distillationdistilled off solvent

Sources & evidence

ORD record
ord-cd047809c58d4e9986b8beddcc9ef952
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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