Water → HCID 77230689, compound

HRID 1519582Notes

Reaction equation

HRID 1519582 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([CH3:11])[CH:4]=1)=[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])=[CH:4][C:5]=1[CH3:11])#[N:8]

Participants

7

Reactant 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 2723922Sodium ethoxideHCID 45083566Benzonitrile, 4-formyl-2-methyl- (9CI)

Product 1

HCID 77230689HCID 77230689, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A mixture of 4-formyl-2-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 5 mL of ethanol was added, and the mixture was stirred at room temperature for 2 hours. The mixture was added water, then extracted with EtOAc. The organic layers were dried over Na2SO4 and concentrated to afford ethyl 3-(4-cyano-3-methylphenyl)oxirane-2-carboxylate. MS m/z: 232 (M+1)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1667dd057a4f4fdbaf6c40525b84f93c
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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