Benzyl Bromide → Ethyl 2-cyano-3-phenylpropanoate

HRID 1655715Notes

Reaction equation

HRID 1655715 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC[O-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:8])[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]#[N:7])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxide

Product 1

HCID 228103Ethyl 2-cyano-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyanoacetic acid ethyl ester was alkylated with benzyl bromide in the presence of sodium ethylate in ethanol to give benzyl-cyanoacetic acid ethyl ester [MS: 203 (M)+ ] which was then subsequently hydrolyzed with 1N sodium hydroxide solution in a 9:1 mixture of methanol and water to give the corresponding acid. Recrystallization of the crude product from methylene chloride/hexane yielded benzyl-cyanoacetic acid as crystals of melting point 97°.

Sources & evidence

ORD record
ord-281acf31a33a48f3889494a81c311132
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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