Ethanol → Ethyl 3-(1-cyanoethyl)benzoate

HRID 564011Notes

Reaction equation

HRID 564011 reaction equation
[C:1]([CH:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])[CH3:4])#[N:2].[C:14](Cl)(=O)[C:15](Cl)=O.C(O)C>ClCCl.CN(C=O)C>[CH2:14]([O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][CH:13]=[C:5]([CH:3]([C:1]#[N:2])[CH3:4])[CH:6]=1)[CH3:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 983703-(1-Cyanoethyl)benzoic acid

Product 1

HCID 67007698Ethyl 3-(1-cyanoethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 700 mg 3-(1-Cyano-ethyl)-benzoic acid in 20 ml dichloromethane were added dropwise 610 mg oxalyl chloride and 2 drops of DMF at RT. After stirring for 1 hr, 10 ml ethanol were added and stirring was continued for another hr. The solvents were evaporated, the residue dissolved in dichloromethane and washed with aqueous sodium bicarbonate solution. The dichloromethane phase was dried, evaporated and the residue purified by chromatography on silica in ethyl acetate/heptane mixtures.

Workup

  1. stirringstirring
  2. waitwas continued for another hr
  3. customThe solvents were evaporated
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed with aqueous sodium bicarbonate solution
  6. dry with materialThe dichloromethane phase was dried
  7. customevaporated
  8. customthe residue purified by chromatography on silica in ethyl acetate/heptane mixtures

Sources & evidence

ORD record
ord-3417beb374594833b8be09383f298f88
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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